Today's Aim

In the Mapper visualisation, make small images of the molecules show up instead of their index in the dataset. This allows everything to look much neater and practical chemists can see what's going on intuitively.

Other Aims:

  1. Use PCA on the fingerprints to identify a few important sections, and use that as the lens.
  2. Use a different colouring function (presence of functional group, max(activity), min(activity), stdev(activity))
  3. For each drug, generate a bitvector of "which target has this been tested on". Then cluster in "drug-target" space using that bitvectorand see what we spot.
  4. For a specific and well-tested target, generate a classifier (e.g. random forest) to predict how effective a drug is against it. Then, use the Fibres of Failure method (Carlsson, L., Carlsson G., Vejdemo-Johansson M., https://arxiv.org/abs/1803.00384 ) to predict when it goes wrong.

Dead Ends:

  1. Highlighting molecules by what they share with the links.

Pitfalls:

  1. Watch out for the lens just discretising the dataset. This will often show up as a ladder in 1D, but make sure to plot it in 2D
In [9]:
import numpy as np
import sklearn
from rdkit import Chem
from rdkit.Chem import AllChem
from rdkit.Chem import rdDepictor
from rdkit.Chem.Draw import rdMolDraw2D
import rdkit.Chem.Fingerprints.ClusterMols
from IPython.display import SVG, IFrame
import gzip
import os
import pickle
import pandas as pd
import kmapper as km
from kmapper import jupyter
from sklearn import cluster
In [10]:
with open("../data/processed/curated_set_with_publication_year.pd.pkl", "rb") as infile:
    df = pickle.load(infile)
In [11]:
from collections import Counter
possible_targets = Counter([item for item in df["TGT_CHEMBL_ID"]])
print(len(possible_targets))
print(len(df))
print(possible_targets)
first_target = df["TGT_CHEMBL_ID"] == "CHEMBL240"
sub_df = df[first_target]

1227
314767
Counter({'CHEMBL240': 4703, 'CHEMBL253': 3472, 'CHEMBL218': 2997, 'CHEMBL251': 2976, 'CHEMBL228': 2853, 'CHEMBL264': 2548, 'CHEMBL226': 2544, 'CHEMBL217': 2473, 'CHEMBL344': 2358, 'CHEMBL243': 2315, 'CHEMBL256': 2304, 'CHEMBL205': 2257, 'CHEMBL279': 2142, 'CHEMBL261': 2089, 'CHEMBL4235': 2020, 'CHEMBL244': 2010, 'CHEMBL222': 2003, 'CHEMBL233': 1998, 'CHEMBL4078': 1994, 'CHEMBL284': 1950, 'CHEMBL237': 1908, 'CHEMBL259': 1828, 'CHEMBL4822': 1799, 'CHEMBL3371': 1773, 'CHEMBL214': 1703, 'CHEMBL313': 1690, 'CHEMBL3594': 1678, 'CHEMBL203': 1659, 'CHEMBL224': 1643, 'CHEMBL4296': 1594, 'CHEMBL260': 1589, 'CHEMBL235': 1575, 'CHEMBL234': 1569, 'CHEMBL225': 1565, 'CHEMBL236': 1550, 'CHEMBL220': 1542, 'CHEMBL238': 1518, 'CHEMBL247': 1474, 'CHEMBL255': 1445, 'CHEMBL3952': 1424, 'CHEMBL2039': 1403, 'CHEMBL340': 1386, 'CHEMBL3242': 1380, 'CHEMBL204': 1347, 'CHEMBL5071': 1332, 'CHEMBL239': 1324, 'CHEMBL325': 1298, 'CHEMBL5763': 1282, 'CHEMBL2034': 1258, 'CHEMBL4015': 1234, 'CHEMBL2409': 1204, 'CHEMBL3227': 1194, 'CHEMBL2954': 1194, 'CHEMBL4354': 1184, 'CHEMBL3229': 1135, 'CHEMBL4794': 1119, 'CHEMBL3571': 1112, 'CHEMBL3717': 1109, 'CHEMBL230': 1104, 'CHEMBL268': 1103, 'CHEMBL338': 1089, 'CHEMBL4153': 1089, 'CHEMBL335': 1076, 'CHEMBL273': 1066, 'CHEMBL270': 1057, 'CHEMBL286': 1052, 'CHEMBL245': 1044, 'CHEMBL274': 1042, 'CHEMBL1914': 1024, 'CHEMBL333': 1001, 'CHEMBL3155': 968, 'CHEMBL2014': 963, 'CHEMBL1951': 961, 'CHEMBL4333': 945, 'CHEMBL3910': 945, 'CHEMBL4005': 923, 'CHEMBL5136': 921, 'CHEMBL339': 916, 'CHEMBL1871': 916, 'CHEMBL3948': 905, 'CHEMBL280': 895, 'CHEMBL2564': 893, 'CHEMBL4616': 887, 'CHEMBL249': 868, 'CHEMBL206': 864, 'CHEMBL3759': 863, 'CHEMBL3105': 845, 'CHEMBL267': 829, 'CHEMBL1978': 827, 'CHEMBL216': 817, 'CHEMBL3979': 805, 'CHEMBL4124': 805, 'CHEMBL3884': 803, 'CHEMBL210': 796, 'CHEMBL2243': 790, 'CHEMBL321': 788, 'CHEMBL1800': 785, 'CHEMBL262': 767, 'CHEMBL4980': 767, 'CHEMBL2001': 763, 'CHEMBL246': 761, 'CHEMBL289': 752, 'CHEMBL3471': 744, 'CHEMBL1824': 736, 'CHEMBL4441': 730, 'CHEMBL208': 713, 'CHEMBL4282': 712, 'CHEMBL2949': 708, 'CHEMBL332': 708, 'CHEMBL219': 705, 'CHEMBL318': 702, 'CHEMBL242': 700, 'CHEMBL1833': 695, 'CHEMBL3837': 692, 'CHEMBL4805': 692, 'CHEMBL5102': 689, 'CHEMBL215': 689, 'CHEMBL213': 679, 'CHEMBL229': 677, 'CHEMBL1865': 664, 'CHEMBL322': 662, 'CHEMBL3222': 657, 'CHEMBL2425': 654, 'CHEMBL3397': 653, 'CHEMBL269': 644, 'CHEMBL4552': 643, 'CHEMBL4308': 641, 'CHEMBL4630': 626, 'CHEMBL6009': 624, 'CHEMBL302': 623, 'CHEMBL4409': 617, 'CHEMBL4561': 613, 'CHEMBL211': 612, 'CHEMBL1855': 606, 'CHEMBL5652': 601, 'CHEMBL2337': 596, 'CHEMBL3769': 586, 'CHEMBL231': 585, 'CHEMBL3820': 582, 'CHEMBL275': 574, 'CHEMBL4581': 572, 'CHEMBL3892': 566, 'CHEMBL2147': 563, 'CHEMBL1926': 561, 'CHEMBL3473': 543, 'CHEMBL1957': 542, 'CHEMBL221': 541, 'CHEMBL1889': 538, 'CHEMBL4072': 535, 'CHEMBL283': 532, 'CHEMBL2842': 532, 'CHEMBL2971': 530, 'CHEMBL3798': 530, 'CHEMBL4722': 525, 'CHEMBL2722': 521, 'CHEMBL2492': 519, 'CHEMBL4481': 516, 'CHEMBL1985': 515, 'CHEMBL4302': 513, 'CHEMBL3199': 507, 'CHEMBL3145': 507, 'CHEMBL258': 505, 'CHEMBL3192': 500, 'CHEMBL2590': 493, 'CHEMBL2334': 491, 'CHEMBL1908': 491, 'CHEMBL3267': 491, 'CHEMBL1811': 485, 'CHEMBL4644': 484, 'CHEMBL5658': 482, 'CHEMBL2208': 478, 'CHEMBL3602': 474, 'CHEMBL4422': 470, 'CHEMBL1827': 468, 'CHEMBL4074': 467, 'CHEMBL2581': 466, 'CHEMBL1991': 465, 'CHEMBL3510': 463, 'CHEMBL4439': 457, 'CHEMBL3785': 455, 'CHEMBL3130': 452, 'CHEMBL2056': 451, 'CHEMBL2326': 448, 'CHEMBL3572': 448, 'CHEMBL5076': 447, 'CHEMBL4306': 445, 'CHEMBL5375': 444, 'CHEMBL3943': 443, 'CHEMBL3710': 443, 'CHEMBL3501': 436, 'CHEMBL2276': 436, 'CHEMBL288': 432, 'CHEMBL4657': 430, 'CHEMBL1862': 424, 'CHEMBL3568': 418, 'CHEMBL2413': 415, 'CHEMBL3706': 414, 'CHEMBL232': 412, 'CHEMBL4102': 411, 'CHEMBL1898': 409, 'CHEMBL4649': 406, 'CHEMBL3869': 405, 'CHEMBL1983': 403, 'CHEMBL3772': 402, 'CHEMBL2047': 400, 'CHEMBL248': 394, 'CHEMBL3563': 394, 'CHEMBL1867': 393, 'CHEMBL1946': 393, 'CHEMBL1974': 393, 'CHEMBL4477': 382, 'CHEMBL1947': 382, 'CHEMBL4523': 380, 'CHEMBL2568': 379, 'CHEMBL4093': 377, 'CHEMBL5555': 376, 'CHEMBL4608': 375, 'CHEMBL5409': 375, 'CHEMBL3975': 374, 'CHEMBL2185': 374, 'CHEMBL3622': 372, 'CHEMBL202': 371, 'CHEMBL2434': 370, 'CHEMBL2993': 370, 'CHEMBL5137': 366, 'CHEMBL3464': 366, 'CHEMBL2808': 363, 'CHEMBL1936': 362, 'CHEMBL4792': 362, 'CHEMBL2858': 361, 'CHEMBL5077': 359, 'CHEMBL3974': 357, 'CHEMBL5424': 357, 'CHEMBL3356': 355, 'CHEMBL1937': 354, 'CHEMBL1878': 352, 'CHEMBL4893': 351, 'CHEMBL1994': 351, 'CHEMBL5023': 350, 'CHEMBL223': 348, 'CHEMBL2916': 345, 'CHEMBL4128': 345, 'CHEMBL5414': 342, 'CHEMBL5441': 339, 'CHEMBL4696': 339, 'CHEMBL4829': 338, 'CHEMBL3358': 335, 'CHEMBL2148': 334, 'CHEMBL1945': 329, 'CHEMBL4979': 326, 'CHEMBL2835': 325, 'CHEMBL4803': 322, 'CHEMBL1899': 319, 'CHEMBL5471': 319, 'CHEMBL2622': 318, 'CHEMBL4768': 318, 'CHEMBL4414': 317, 'CHEMBL4247': 314, 'CHEMBL4429': 314, 'CHEMBL2851': 314, 'CHEMBL1821': 311, 'CHEMBL2335': 311, 'CHEMBL1744525': 310, 'CHEMBL2695': 307, 'CHEMBL4303': 306, 'CHEMBL3181': 305, 'CHEMBL3795': 304, 'CHEMBL1875': 304, 'CHEMBL2973': 303, 'CHEMBL4793': 302, 'CHEMBL299': 299, 'CHEMBL3138': 299, 'CHEMBL5113': 297, 'CHEMBL2304404': 296, 'CHEMBL2049': 294, 'CHEMBL1829': 292, 'CHEMBL3012': 291, 'CHEMBL5145': 291, 'CHEMBL3286': 290, 'CHEMBL4618': 289, 'CHEMBL304': 288, 'CHEMBL2035': 288, 'CHEMBL3922': 288, 'CHEMBL4321': 288, 'CHEMBL1790': 286, 'CHEMBL3048': 285, 'CHEMBL2959': 284, 'CHEMBL4315': 282, 'CHEMBL3729': 282, 'CHEMBL3230': 282, 'CHEMBL3768': 281, 'CHEMBL254': 280, 'CHEMBL4681': 279, 'CHEMBL3976': 279, 'CHEMBL3649': 279, 'CHEMBL2782': 279, 'CHEMBL4427': 275, 'CHEMBL312': 274, 'CHEMBL4198': 273, 'CHEMBL2496': 272, 'CHEMBL4588': 271, 'CHEMBL4191': 270, 'CHEMBL3880': 270, 'CHEMBL4462': 269, 'CHEMBL3318': 267, 'CHEMBL2789': 267, 'CHEMBL4077': 266, 'CHEMBL3942': 265, 'CHEMBL1836': 265, 'CHEMBL4698': 264, 'CHEMBL3474': 258, 'CHEMBL4685': 258, 'CHEMBL5036': 256, 'CHEMBL5353': 255, 'CHEMBL1900': 254, 'CHEMBL1916': 254, 'CHEMBL1868': 254, 'CHEMBL5192': 254, 'CHEMBL1913': 251, 'CHEMBL6007': 251, 'CHEMBL4777': 249, 'CHEMBL3587': 247, 'CHEMBL4361': 247, 'CHEMBL3142': 247, 'CHEMBL4179': 246, 'CHEMBL3468': 245, 'CHEMBL5373': 245, 'CHEMBL1952': 244, 'CHEMBL4975': 241, 'CHEMBL2470': 241, 'CHEMBL2599': 240, 'CHEMBL4789': 239, 'CHEMBL2637': 239, 'CHEMBL311': 238, 'CHEMBL4625': 237, 'CHEMBL2996': 236, 'CHEMBL2363': 236, 'CHEMBL3231': 236, 'CHEMBL5498': 235, 'CHEMBL2882': 235, 'CHEMBL1921': 235, 'CHEMBL265': 233, 'CHEMBL3025': 232, 'CHEMBL5393': 229, 'CHEMBL5017': 228, 'CHEMBL5067': 228, 'CHEMBL2292': 228, 'CHEMBL4111': 227, 'CHEMBL4860': 227, 'CHEMBL4801': 225, 'CHEMBL5491': 225, 'CHEMBL5567': 225, 'CHEMBL2002': 225, 'CHEMBL3524': 225, 'CHEMBL4372': 225, 'CHEMBL1844': 224, 'CHEMBL5669': 224, 'CHEMBL4080': 223, 'CHEMBL5508': 223, 'CHEMBL4393': 221, 'CHEMBL3807': 221, 'CHEMBL287': 218, 'CHEMBL1966': 217, 'CHEMBL2431': 217, 'CHEMBL2285': 216, 'CHEMBL2414': 215, 'CHEMBL4506': 214, 'CHEMBL1942': 213, 'CHEMBL3650': 213, 'CHEMBL276': 213, 'CHEMBL6184': 213, 'CHEMBL1860': 212, 'CHEMBL4398': 212, 'CHEMBL2567': 212, 'CHEMBL2069': 211, 'CHEMBL3522': 210, 'CHEMBL5131': 207, 'CHEMBL5160': 206, 'CHEMBL3815': 205, 'CHEMBL3332': 205, 'CHEMBL1741186': 205, 'CHEMBL319': 204, 'CHEMBL5971': 202, 'CHEMBL326': 201, 'CHEMBL3351': 201, 'CHEMBL2730': 201, 'CHEMBL4336': 199, 'CHEMBL227': 198, 'CHEMBL2778': 198, 'CHEMBL3066': 197, 'CHEMBL1801': 196, 'CHEMBL1980': 196, 'CHEMBL2329': 195, 'CHEMBL2575': 195, 'CHEMBL1075228': 195, 'CHEMBL3764': 195, 'CHEMBL2327': 193, 'CHEMBL1849': 193, 'CHEMBL4780': 191, 'CHEMBL2736': 190, 'CHEMBL1792': 190, 'CHEMBL5457': 188, 'CHEMBL301': 188, 'CHEMBL4641': 188, 'CHEMBL6137': 187, 'CHEMBL3912': 187, 'CHEMBL5387': 186, 'CHEMBL3969': 185, 'CHEMBL2107': 185, 'CHEMBL2871': 184, 'CHEMBL4699': 184, 'CHEMBL1163125': 184, 'CHEMBL2016': 182, 'CHEMBL3959': 181, 'CHEMBL324': 180, 'CHEMBL2028': 180, 'CHEMBL4550': 180, 'CHEMBL2373': 180, 'CHEMBL1901': 179, 'CHEMBL4132': 179, 'CHEMBL1795101': 176, 'CHEMBL3081': 176, 'CHEMBL3247': 176, 'CHEMBL1075140': 176, 'CHEMBL5443': 176, 'CHEMBL5445': 176, 'CHEMBL1864': 175, 'CHEMBL5314': 173, 'CHEMBL2274': 173, 'CHEMBL2525': 173, 'CHEMBL1075104': 172, 'CHEMBL2830': 172, 'CHEMBL2203': 172, 'CHEMBL3223': 170, 'CHEMBL5328': 169, 'CHEMBL4508': 169, 'CHEMBL4471': 168, 'CHEMBL4234': 168, 'CHEMBL1941': 165, 'CHEMBL4016': 165, 'CHEMBL4596': 165, 'CHEMBL5407': 165, 'CHEMBL2265': 163, 'CHEMBL2756': 163, 'CHEMBL4802': 163, 'CHEMBL3018': 161, 'CHEMBL3920': 160, 'CHEMBL4018': 160, 'CHEMBL2781': 159, 'CHEMBL1255149': 159, 'CHEMBL241': 158, 'CHEMBL4026': 158, 'CHEMBL3024': 158, 'CHEMBL5800': 157, 'CHEMBL4261': 156, 'CHEMBL1977': 156, 'CHEMBL4714': 156, 'CHEMBL3403': 155, 'CHEMBL3589': 153, 'CHEMBL4073': 152, 'CHEMBL4161': 152, 'CHEMBL6145': 152, 'CHEMBL1997': 151, 'CHEMBL4068': 150, 'CHEMBL6136': 150, 'CHEMBL2489': 149, 'CHEMBL5263': 149, 'CHEMBL3816': 148, 'CHEMBL4652': 148, 'CHEMBL3045': 147, 'CHEMBL5251': 145, 'CHEMBL6154': 145, 'CHEMBL3746': 145, 'CHEMBL4040': 145, 'CHEMBL1850': 145, 'CHEMBL4895': 144, 'CHEMBL3553': 144, 'CHEMBL1075189': 144, 'CHEMBL4617': 143, 'CHEMBL5697': 143, 'CHEMBL3486': 143, 'CHEMBL309': 142, 'CHEMBL2459': 142, 'CHEMBL3254': 142, 'CHEMBL4828': 142, 'CHEMBL1892': 140, 'CHEMBL2487': 140, 'CHEMBL4804': 139, 'CHEMBL4188': 139, 'CHEMBL3157': 137, 'CHEMBL1856': 136, 'CHEMBL1902': 136, 'CHEMBL4633': 136, 'CHEMBL2061': 136, 'CHEMBL278': 135, 'CHEMBL1906': 134, 'CHEMBL4051': 134, 'CHEMBL3106': 134, 'CHEMBL5011': 133, 'CHEMBL6164': 132, 'CHEMBL3629': 132, 'CHEMBL3559': 131, 'CHEMBL2474': 130, 'CHEMBL4653': 130, 'CHEMBL2815': 130, 'CHEMBL1075284': 129, 'CHEMBL4465': 129, 'CHEMBL5857': 128, 'CHEMBL2902': 128, 'CHEMBL2041': 128, 'CHEMBL4816': 128, 'CHEMBL1075051': 128, 'CHEMBL1293267': 128, 'CHEMBL3891': 127, 'CHEMBL1293255': 127, 'CHEMBL4394': 127, 'CHEMBL4140': 127, 'CHEMBL2978': 127, 'CHEMBL1806': 126, 'CHEMBL5720': 125, 'CHEMBL4150': 125, 'CHEMBL2652': 125, 'CHEMBL2085': 124, 'CHEMBL2007': 124, 'CHEMBL1981': 124, 'CHEMBL5570': 123, 'CHEMBL5631': 122, 'CHEMBL3437': 122, 'CHEMBL3359': 122, 'CHEMBL3582': 121, 'CHEMBL2803': 121, 'CHEMBL1881': 121, 'CHEMBL4329': 121, 'CHEMBL5936': 121, 'CHEMBL2716': 120, 'CHEMBL3753': 120, 'CHEMBL3991': 119, 'CHEMBL1822': 119, 'CHEMBL1163116': 118, 'CHEMBL3426': 118, 'CHEMBL5462': 118, 'CHEMBL2123': 118, 'CHEMBL1781862': 118, 'CHEMBL1907': 117, 'CHEMBL3060': 117, 'CHEMBL2499': 117, 'CHEMBL1944': 116, 'CHEMBL4899': 116, 'CHEMBL3775': 116, 'CHEMBL6140': 116, 'CHEMBL2361': 116, 'CHEMBL4919': 115, 'CHEMBL1995': 115, 'CHEMBL3699': 115, 'CHEMBL5582': 114, 'CHEMBL5331': 114, 'CHEMBL4383': 114, 'CHEMBL4662': 114, 'CHEMBL2288': 114, 'CHEMBL3314': 113, 'CHEMBL1804': 113, 'CHEMBL5485': 113, 'CHEMBL3037': 113, 'CHEMBL3202': 113, 'CHEMBL2903': 113, 'CHEMBL6080': 113, 'CHEMBL2820': 113, 'CHEMBL2366456': 113, 'CHEMBL2336': 112, 'CHEMBL308': 112, 'CHEMBL3691': 112, 'CHEMBL1667665': 111, 'CHEMBL1782': 111, 'CHEMBL4468': 111, 'CHEMBL6084': 111, 'CHEMBL2617': 111, 'CHEMBL1255150': 111, 'CHEMBL3655': 110, 'CHEMBL3766': 110, 'CHEMBL4123': 110, 'CHEMBL5282': 109, 'CHEMBL3687': 109, 'CHEMBL5525': 109, 'CHEMBL5221': 109, 'CHEMBL4224': 108, 'CHEMBL2534': 108, 'CHEMBL2397': 108, 'CHEMBL3776': 106, 'CHEMBL5704': 106, 'CHEMBL5306': 106, 'CHEMBL1075319': 106, 'CHEMBL4338': 105, 'CHEMBL5769': 105, 'CHEMBL2391': 104, 'CHEMBL2868': 103, 'CHEMBL3401': 103, 'CHEMBL3780': 103, 'CHEMBL2536': 102, 'CHEMBL3623': 102, 'CHEMBL2885': 102, 'CHEMBL4824': 102, 'CHEMBL5767': 101, 'CHEMBL2461': 101, 'CHEMBL3868': 101, 'CHEMBL2366512': 101, 'CHEMBL4729': 100, 'CHEMBL5205': 99, 'CHEMBL3180': 98, 'CHEMBL3921': 98, 'CHEMBL5847': 98, 'CHEMBL1873': 98, 'CHEMBL3305': 98, 'CHEMBL3361': 98, 'CHEMBL2734': 98, 'CHEMBL2611': 98, 'CHEMBL2725': 98, 'CHEMBL3864': 97, 'CHEMBL4029': 97, 'CHEMBL2083': 97, 'CHEMBL4478': 97, 'CHEMBL2046264': 97, 'CHEMBL4687': 96, 'CHEMBL4779': 96, 'CHEMBL2069161': 96, 'CHEMBL4203': 95, 'CHEMBL3360': 95, 'CHEMBL3721': 95, 'CHEMBL2828': 94, 'CHEMBL4908': 94, 'CHEMBL1287623': 94, 'CHEMBL4761': 94, 'CHEMBL3802': 94, 'CHEMBL1795126': 94, 'CHEMBL1798': 93, 'CHEMBL5973': 93, 'CHEMBL2488': 93, 'CHEMBL1075138': 93, 'CHEMBL2447': 93, 'CHEMBL5662': 93, 'CHEMBL5337': 92, 'CHEMBL4835': 92, 'CHEMBL4086': 92, 'CHEMBL1075145': 92, 'CHEMBL2563': 91, 'CHEMBL3263': 91, 'CHEMBL2027': 91, 'CHEMBL3166': 90, 'CHEMBL3819': 90, 'CHEMBL5543': 90, 'CHEMBL4791': 90, 'CHEMBL1955': 90, 'CHEMBL4090': 89, 'CHEMBL5619': 89, 'CHEMBL1917': 89, 'CHEMBL4145': 89, 'CHEMBL2693': 89, 'CHEMBL4586': 89, 'CHEMBL3898': 89, 'CHEMBL1926488': 89, 'CHEMBL315': 88, 'CHEMBL2787': 88, 'CHEMBL5203': 88, 'CHEMBL1808': 87, 'CHEMBL3313': 87, 'CHEMBL3983': 87, 'CHEMBL5141': 86, 'CHEMBL3348': 86, 'CHEMBL252': 85, 'CHEMBL2490': 85, 'CHEMBL5575': 85, 'CHEMBL3310': 85, 'CHEMBL4767': 85, 'CHEMBL2919': 84, 'CHEMBL4489': 84, 'CHEMBL3719': 84, 'CHEMBL320': 84, 'CHEMBL3514': 84, 'CHEMBL4430': 83, 'CHEMBL2252': 83, 'CHEMBL4921': 83, 'CHEMBL2366517': 83, 'CHEMBL3616': 82, 'CHEMBL3198': 82, 'CHEMBL3455': 82, 'CHEMBL1287622': 82, 'CHEMBL2411': 82, 'CHEMBL2982': 81, 'CHEMBL401': 81, 'CHEMBL3476': 81, 'CHEMBL2345': 81, 'CHEMBL5162': 81, 'CHEMBL209': 80, 'CHEMBL2938': 80, 'CHEMBL5785': 80, 'CHEMBL5147': 80, 'CHEMBL5103': 80, 'CHEMBL3321': 80, 'CHEMBL5200': 80, 'CHEMBL1169598': 80, 'CHEMBL1795180': 80, 'CHEMBL2186': 79, 'CHEMBL4304': 79, 'CHEMBL1853': 78, 'CHEMBL5451': 78, 'CHEMBL291': 78, 'CHEMBL5158': 78, 'CHEMBL6056': 78, 'CHEMBL3637': 77, 'CHEMBL3160': 77, 'CHEMBL3252': 77, 'CHEMBL5351': 77, 'CHEMBL4227': 77, 'CHEMBL3478': 76, 'CHEMBL1795127': 76, 'CHEMBL1293293': 76, 'CHEMBL281': 76, 'CHEMBL2366461': 76, 'CHEMBL4530': 76, 'CHEMBL2749': 75, 'CHEMBL285': 75, 'CHEMBL3933': 75, 'CHEMBL3117': 75, 'CHEMBL3072': 74, 'CHEMBL4358': 74, 'CHEMBL3513': 74, 'CHEMBL4158': 74, 'CHEMBL4497': 74, 'CHEMBL5035': 74, 'CHEMBL3338': 73, 'CHEMBL3998': 73, 'CHEMBL2366481': 73, 'CHEMBL3349': 73, 'CHEMBL2810': 73, 'CHEMBL5299': 73, 'CHEMBL4556': 72, 'CHEMBL5517': 72, 'CHEMBL2577': 72, 'CHEMBL4033': 72, 'CHEMBL5185': 72, 'CHEMBL3085613': 72, 'CHEMBL3272': 71, 'CHEMBL1787': 71, 'CHEMBL2231': 71, 'CHEMBL2181': 71, 'CHEMBL1859': 71, 'CHEMBL5413': 71, 'CHEMBL1904': 71, 'CHEMBL2998': 71, 'CHEMBL5402': 70, 'CHEMBL1918': 70, 'CHEMBL3243909': 69, 'CHEMBL3788': 69, 'CHEMBL3085': 69, 'CHEMBL1795135': 69, 'CHEMBL5028': 69, 'CHEMBL3114': 69, 'CHEMBL5533': 69, 'CHEMBL3067': 69, 'CHEMBL6141': 68, 'CHEMBL1784': 68, 'CHEMBL5360': 68, 'CHEMBL3548': 68, 'CHEMBL4903': 68, 'CHEMBL2526': 67, 'CHEMBL5493': 67, 'CHEMBL4769': 67, 'CHEMBL4027': 67, 'CHEMBL2179': 67, 'CHEMBL1681620': 66, 'CHEMBL3897': 66, 'CHEMBL5905': 66, 'CHEMBL4391': 66, 'CHEMBL2360': 66, 'CHEMBL2527': 65, 'CHEMBL2000': 65, 'CHEMBL5852': 65, 'CHEMBL3508': 64, 'CHEMBL2664': 64, 'CHEMBL5189': 64, 'CHEMBL2065': 64, 'CHEMBL1293244': 64, 'CHEMBL5281': 64, 'CHEMBL3813': 64, 'CHEMBL1770046': 64, 'CHEMBL1075152': 64, 'CHEMBL3541': 63, 'CHEMBL4237': 63, 'CHEMBL2304401': 63, 'CHEMBL3250': 63, 'CHEMBL2366408': 63, 'CHEMBL3374': 63, 'CHEMBL3905': 63, 'CHEMBL2480': 63, 'CHEMBL329': 63, 'CHEMBL3833': 63, 'CHEMBL5685': 63, 'CHEMBL5031': 63, 'CHEMBL1949': 63, 'CHEMBL1293292': 63, 'CHEMBL3927': 62, 'CHEMBL3438': 62, 'CHEMBL1795139': 62, 'CHEMBL3996': 61, 'CHEMBL3459': 60, 'CHEMBL298': 60, 'CHEMBL3004': 60, 'CHEMBL5319': 60, 'CHEMBL2318': 60, 'CHEMBL3614': 60, 'CHEMBL3475': 60, 'CHEMBL6165': 60, 'CHEMBL5832': 60, 'CHEMBL1275212': 60, 'CHEMBL1785': 59, 'CHEMBL2331': 59, 'CHEMBL5062': 59, 'CHEMBL3961': 59, 'CHEMBL1781': 59, 'CHEMBL6069': 59, 'CHEMBL4133': 59, 'CHEMBL2380186': 59, 'CHEMBL2104': 59, 'CHEMBL5630': 58, 'CHEMBL4973': 58, 'CHEMBL1293222': 58, 'CHEMBL3429': 58, 'CHEMBL4081': 58, 'CHEMBL4376': 58, 'CHEMBL4062': 58, 'CHEMBL6032': 58, 'CHEMBL1075280': 58, 'CHEMBL5500': 58, 'CHEMBL4773': 58, 'CHEMBL3023': 58, 'CHEMBL4267': 57, 'CHEMBL4187': 57, 'CHEMBL2246': 57, 'CHEMBL5419': 57, 'CHEMBL1795117': 57, 'CHEMBL2135': 57, 'CHEMBL3565': 56, 'CHEMBL2424': 56, 'CHEMBL4317': 56, 'CHEMBL2850': 56, 'CHEMBL2034805': 56, 'CHEMBL4683': 56, 'CHEMBL5440': 56, 'CHEMBL3490': 56, 'CHEMBL1743125': 55, 'CHEMBL5122': 55, 'CHEMBL3419': 55, 'CHEMBL4878': 55, 'CHEMBL2635': 55, 'CHEMBL2721': 54, 'CHEMBL2528': 54, 'CHEMBL4542': 54, 'CHEMBL1163111': 54, 'CHEMBL3902': 54, 'CHEMBL1903': 54, 'CHEMBL5869': 54, 'CHEMBL3056': 54, 'CHEMBL1075322': 54, 'CHEMBL3337': 54, 'CHEMBL4983': 54, 'CHEMBL5024': 54, 'CHEMBL1993': 53, 'CHEMBL1929': 52, 'CHEMBL2073': 52, 'CHEMBL4599': 52, 'CHEMBL4774': 52, 'CHEMBL3392': 52, 'CHEMBL4892': 52, 'CHEMBL5776': 52, 'CHEMBL4228': 52, 'CHEMBL4848': 52, 'CHEMBL5378': 52, 'CHEMBL3368': 52, 'CHEMBL1921666': 52, 'CHEMBL2967': 51, 'CHEMBL3433': 51, 'CHEMBL250': 51, 'CHEMBL290': 51, 'CHEMBL4305': 51, 'CHEMBL1075214': 51, 'CHEMBL4631': 50, 'CHEMBL3564': 50, 'CHEMBL3863': 50, 'CHEMBL1743122': 50, 'CHEMBL2860': 50, 'CHEMBL1615381': 50, 'CHEMBL4941': 50, 'CHEMBL4518': 50, 'CHEMBL5963': 50, 'CHEMBL5850': 50, 'CHEMBL3190': 50, 'CHEMBL2955': 49, 'CHEMBL1968': 49, 'CHEMBL5932': 49, 'CHEMBL5285': 49, 'CHEMBL2378': 49, 'CHEMBL4370': 49, 'CHEMBL3744': 48, 'CHEMBL2634': 48, 'CHEMBL4070': 48, 'CHEMBL1075294': 48, 'CHEMBL5983': 48, 'CHEMBL2128': 48, 'CHEMBL2552': 48, 'CHEMBL5724': 48, 'CHEMBL2129': 48, 'CHEMBL1795167': 48, 'CHEMBL1835': 47, 'CHEMBL4931': 47, 'CHEMBL4211': 47, 'CHEMBL1743126': 47, 'CHEMBL4017': 47, 'CHEMBL5070': 47, 'CHEMBL5359': 47, 'CHEMBL2706': 47, 'CHEMBL4909': 47, 'CHEMBL5868': 47, 'CHEMBL2010631': 47, 'CHEMBL5786': 47, 'CHEMBL3783': 47, 'CHEMBL3738': 47, 'CHEMBL1075108': 47, 'CHEMBL6166': 46, 'CHEMBL3503': 46, 'CHEMBL5774': 46, 'CHEMBL1803': 46, 'CHEMBL1293289': 46, 'CHEMBL4114': 46, 'CHEMBL5255': 46, 'CHEMBL4000': 46, 'CHEMBL3754': 45, 'CHEMBL5038': 45, 'CHEMBL402': 45, 'CHEMBL5879': 45, 'CHEMBL1987': 45, 'CHEMBL1649054': 45, 'CHEMBL4420': 45, 'CHEMBL5464': 45, 'CHEMBL4677': 45, 'CHEMBL1944499': 44, 'CHEMBL3666': 44, 'CHEMBL1795138': 44, 'CHEMBL4461': 44, 'CHEMBL5686': 44, 'CHEMBL2366': 43, 'CHEMBL323': 43, 'CHEMBL3150': 43, 'CHEMBL3308': 43, 'CHEMBL2569': 43, 'CHEMBL2010635': 43, 'CHEMBL6068': 42, 'CHEMBL4580': 42, 'CHEMBL1075269': 42, 'CHEMBL3949': 42, 'CHEMBL3482': 41, 'CHEMBL4840': 41, 'CHEMBL4601': 41, 'CHEMBL4343': 41, 'CHEMBL2878': 41, 'CHEMBL3836': 41, 'CHEMBL3593': 41, 'CHEMBL2189110': 41, 'CHEMBL4079': 41, 'CHEMBL4566': 40, 'CHEMBL2283': 40, 'CHEMBL1075028': 40, 'CHEMBL5938': 40, 'CHEMBL1255165': 40, 'CHEMBL4605': 40, 'CHEMBL6172': 40, 'CHEMBL2889': 40, 'CHEMBL2021745': 40, 'CHEMBL1641347': 39, 'CHEMBL1628461': 39, 'CHEMBL3778': 39, 'CHEMBL3935': 39, 'CHEMBL5952': 39, 'CHEMBL2755': 39, 'CHEMBL5101': 39, 'CHEMBL3345': 39, 'CHEMBL4208': 39, 'CHEMBL310': 39, 'CHEMBL2052039': 39, 'CHEMBL5931': 38, 'CHEMBL2073676': 38, 'CHEMBL3663': 38, 'CHEMBL4225': 38, 'CHEMBL2578': 38, 'CHEMBL331': 38, 'CHEMBL2458': 38, 'CHEMBL5695': 38, 'CHEMBL2439': 38, 'CHEMBL3253': 38, 'CHEMBL6169': 38, 'CHEMBL2898': 38, 'CHEMBL3736': 38, 'CHEMBL5831': 38, 'CHEMBL2514': 38, 'CHEMBL1914272': 38, 'CHEMBL2052038': 38, 'CHEMBL257': 37, 'CHEMBL2289': 37, 'CHEMBL4600': 37, 'CHEMBL2443': 37, 'CHEMBL1075111': 37, 'CHEMBL5951': 37, 'CHEMBL3972': 37, 'CHEMBL4901': 37, 'CHEMBL3817': 37, 'CHEMBL3100': 37, 'CHEMBL3492': 37, 'CHEMBL5048': 37, 'CHEMBL5747': 37, 'CHEMBL2980': 36, 'CHEMBL1841': 36, 'CHEMBL3344': 36, 'CHEMBL4444': 36, 'CHEMBL1908385': 36, 'CHEMBL3326': 36, 'CHEMBL5865': 36, 'CHEMBL5010': 36, 'CHEMBL5538': 36, 'CHEMBL3569': 36, 'CHEMBL2088': 36, 'CHEMBL3656': 36, 'CHEMBL4592': 36, 'CHEMBL1764940': 36, 'CHEMBL4573': 35, 'CHEMBL2888': 35, 'CHEMBL4540': 35, 'CHEMBL5347': 35, 'CHEMBL3529': 35, 'CHEMBL5469': 35, 'CHEMBL3122': 35, 'CHEMBL4087': 35, 'CHEMBL5107': 35, 'CHEMBL6095': 35, 'CHEMBL1944497': 35, 'CHEMBL2046259': 35, 'CHEMBL3636': 35, 'CHEMBL4977': 35, 'CHEMBL4320': 35, 'CHEMBL4731': 34, 'CHEMBL4972': 34, 'CHEMBL4036': 34, 'CHEMBL4501': 34, 'CHEMBL3985': 34, 'CHEMBL3578': 34, 'CHEMBL5536': 34, 'CHEMBL4342': 34, 'CHEMBL3251': 34, 'CHEMBL3545': 34, 'CHEMBL5381': 34, 'CHEMBL3728': 34, 'CHEMBL4335': 34, 'CHEMBL2010636': 34, 'CHEMBL6115': 34, 'CHEMBL6005': 33, 'CHEMBL4527': 33, 'CHEMBL4554': 33, 'CHEMBL3369': 33, 'CHEMBL3009': 33, 'CHEMBL2068': 33, 'CHEMBL3733': 33, 'CHEMBL5756': 33, 'CHEMBL1075307': 33, 'CHEMBL2864': 33, 'CHEMBL5805': 33, 'CHEMBL5401': 33, 'CHEMBL3218': 33, 'CHEMBL4619': 33, 'CHEMBL4360': 33, 'CHEMBL2966': 32, 'CHEMBL3835': 32, 'CHEMBL5335': 32, 'CHEMBL4421': 32, 'CHEMBL1075069': 32, 'CHEMBL4400': 32, 'CHEMBL3535': 32, 'CHEMBL3799': 32, 'CHEMBL1293224': 32, 'CHEMBL3148': 32, 'CHEMBL1741220': 32, 'CHEMBL4940': 32, 'CHEMBL2794': 32, 'CHEMBL5262': 32, 'CHEMBL3646': 31, 'CHEMBL4426': 31, 'CHEMBL5270': 31, 'CHEMBL3849': 31, 'CHEMBL1075246': 31, 'CHEMBL3480': 31, 'CHEMBL5888': 31, 'CHEMBL2200': 31, 'CHEMBL3383': 31, 'CHEMBL4760': 31, 'CHEMBL3688': 31, 'CHEMBL1075305': 31, 'CHEMBL2593': 31, 'CHEMBL2570': 31, 'CHEMBL2738': 31, 'CHEMBL2573': 30, 'CHEMBL3924': 30, 'CHEMBL3911': 30, 'CHEMBL3561': 30, 'CHEMBL3640': 30, 'CHEMBL3751': 30, 'CHEMBL3504': 30, 'CHEMBL1075282': 30, 'CHEMBL4162': 30, 'CHEMBL5114': 30, 'CHEMBL3325': 29, 'CHEMBL2964': 29, 'CHEMBL2468': 29, 'CHEMBL4014': 29, 'CHEMBL5545': 29, 'CHEMBL4701': 29, 'CHEMBL2073670': 29, 'CHEMBL2372': 29, 'CHEMBL5784': 29, 'CHEMBL5657': 29, 'CHEMBL4098': 29, 'CHEMBL3577': 29, 'CHEMBL2718': 29, 'CHEMBL1795119': 29, 'CHEMBL2052028': 29, 'CHEMBL5431': 29, 'CHEMBL3234': 28, 'CHEMBL2560': 28, 'CHEMBL4897': 28, 'CHEMBL6029': 28, 'CHEMBL1075024': 28, 'CHEMBL2051': 28, 'CHEMBL1938210': 28, 'CHEMBL3505': 28, 'CHEMBL5161': 28, 'CHEMBL5163': 28, 'CHEMBL2553': 27, 'CHEMBL3607': 27, 'CHEMBL2407': 27, 'CHEMBL2250': 27, 'CHEMBL4454': 27, 'CHEMBL5332': 27, 'CHEMBL1743127': 27, 'CHEMBL4482': 27, 'CHEMBL4898': 27, 'CHEMBL5080': 27, 'CHEMBL2439944': 27, 'CHEMBL4937': 26, 'CHEMBL6120': 26, 'CHEMBL4223': 26, 'CHEMBL4202': 26, 'CHEMBL2717': 26, 'CHEMBL5408': 26, 'CHEMBL317': 26, 'CHEMBL2343': 26, 'CHEMBL5412': 26, 'CHEMBL1649052': 26, 'CHEMBL1795186': 26, 'CHEMBL5366': 25, 'CHEMBL6100': 25, 'CHEMBL2383': 25, 'CHEMBL3116': 25, 'CHEMBL4447': 25, 'CHEMBL1075061': 25, 'CHEMBL5014': 24, 'CHEMBL3981': 24, 'CHEMBL4355': 24, 'CHEMBL3932': 24, 'CHEMBL1770032': 24, 'CHEMBL3467': 24, 'CHEMBL5106': 24, 'CHEMBL1697668': 23, 'CHEMBL2742': 23, 'CHEMBL2708': 23, 'CHEMBL2055': 23, 'CHEMBL1163101': 22, 'CHEMBL2872': 22, 'CHEMBL307': 22, 'CHEMBL5636': 22, 'CHEMBL5845': 22, 'CHEMBL5705': 22, 'CHEMBL5579': 21, 'CHEMBL4954': 21, 'CHEMBL4142': 21, 'CHEMBL3724': 21, 'CHEMBL4708': 20, 'CHEMBL4852': 19, 'CHEMBL4526': 19, 'CHEMBL3055': 19, 'CHEMBL4564': 19, 'CHEMBL1293287': 19, 'CHEMBL5738': 18, 'CHEMBL5627': 18, 'CHEMBL4204': 18, 'CHEMBL2935': 18, 'CHEMBL3246': 18, 'CHEMBL4367': 17, 'CHEMBL5274': 17, 'CHEMBL4151': 17, 'CHEMBL4597': 16, 'CHEMBL3906': 16, 'CHEMBL2801': 16, 'CHEMBL5072': 15, 'CHEMBL3987': 15, 'CHEMBL4134': 15, 'CHEMBL3125': 15, 'CHEMBL2473': 15, 'CHEMBL5749': 14, 'CHEMBL3830': 14, 'CHEMBL4226': 14, 'CHEMBL4924': 14, 'CHEMBL2804': 14, 'CHEMBL4522': 13, 'CHEMBL5698': 13, 'CHEMBL3354': 13, 'CHEMBL5284': 12, 'CHEMBL2349': 11, 'CHEMBL5476': 9, 'CHEMBL5330': 4, 'CHEMBL3357': 4, 'CHEMBL5836': 1, 'CHEMBL4948': 1})
In [12]:
fingerprint_data = [AllChem.GetMorganFingerprintAsBitVect(Chem.MolFromSmiles(smiles),3) for smiles in sub_df["SMILES"]]
try:
    sub_df.insert(0, "FINGERPRINT",fingerprint_data)
except ValueError:
    # If we re-run this cell, we can't reinsert the data (so instead we just replace it)
    sub_df.loc["FINGERPRINT"] = fingerprint_data
In [13]:
sub_df
Out[13]:
FINGERPRINT BIOACT_PCHEMBL_VALUE CMP_ACD_LOGD CMP_ACD_LOGP CMP_ALOGP CMP_AROMATIC_RINGS CMP_CHEMBL_ID CMP_FULL_MWT CMP_HBA CMP_HBD ... CMP_STANDARD_INCHI_KEY CMP_STRUCTURE_TYPE CMP_TYPE_PROTEIN CMP_TYPE_SMALL_MOLECULE DOC_YEAR SMILES TC_key TGT_CHEMBL_ID TGT_ORGANISM TGT_TID
CHEMBL240 - CHEMBL167779 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 1, 0, 1, 0, ... 6.740 3.70 5.85 6.48 3 CHEMBL167779 405.96 2 0 ... GKIRPKYJQBWNGO-QPLCGJKRSA-N MOL False True 2011 CCN(CC)CCOc1ccc(/C(=C(\Cl)c2ccccc2)c2ccccc2)cc1 CHEMBL240 - CHEMBL167779 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL351231 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 6.100 2.80 5.37 4.77 3 CHEMBL351231 330.42 2 0 ... KFHYZKCRXNRKRC-MRXNPFEDSA-N MOL False True 2010 C[C@@H]1CCCN1CCc1cc2cc(-c3ccc(C#N)cc3)ccc2o1 CHEMBL240 - CHEMBL351231 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL61536 [0, 0, 0, 0, 1, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 6.260 0.26 1.31 3.70 3 CHEMBL61536 512.69 4 0 ... YFEPUDFZMYDTMF-UHFFFAOYSA-N MOL False True 2008 Cc1cc[n+]([O-])c(C)c1C(=O)N1CCC(C)(N2CCC(N(Cc3... CHEMBL240 - CHEMBL61536 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL175832 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 5.250 4.53 4.55 4.68 2 CHEMBL175832 401.42 3 0 ... VDURQHWFSXZAER-UHFFFAOYSA-N MOL False True 2005 O=S(=O)(c1ccc(F)cc1)C1(F)CCN(CCc2ccc(F)cc2F)CC1 CHEMBL240 - CHEMBL175832 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL1671889 [0, 0, 0, 0, 0, 1, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 5.220 1.51 1.67 1.33 3 CHEMBL1671889 479.33 6 1 ... UMNUGEIXQBLVCO-UHFFFAOYSA-N MOL False True 2011 N#Cc1ccc(Cn2cncc2CNC2CCN(C(=O)c3cncc(Br)c3)C2=... CHEMBL240 - CHEMBL1671889 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL1671908 [0, 0, 0, 0, 0, 0, 0, 0, 0, 1, 0, 0, 0, 1, 0, ... 4.130 1.46 3.40 4.07 1 CHEMBL1671908 489.63 5 3 ... YTQSVAKKJXBNDL-UHFFFAOYSA-N MOL False True 2011 CCC1=C(C)CC(C(=O)NCCc2ccc(S(=O)(=O)NC(=O)NC3CC... CHEMBL240 - CHEMBL1671908 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL1649912 [0, 1, 0, 0, 0, 1, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 5.370 2.96 5.30 4.01 2 CHEMBL1649912 513.67 4 1 ... PTUIAFZYMVYAII-QUMGSSFMSA-N MOL False True 2011 Cc1nc(C(C)C)n([C@@H]2C[C@@H]3CC[C@H](C2)N3CC[C... CHEMBL240 - CHEMBL1649912 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL1683351 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 5.130 -1.63 1.98 -1.63 1 CHEMBL1683351 388.42 6 1 ... CACJJIUIFBOUQZ-UHFFFAOYSA-N MOL False True 2010 N#Cc1ccc(N2CCN(Cc3cc(C(=O)O)c(=O)n4ccccc34)CC2... CHEMBL240 - CHEMBL1683351 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL1672351 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 5.230 3.17 3.92 4.52 3 CHEMBL1672351 367.46 3 2 ... WFOBNYAVMIYRCG-UHFFFAOYSA-N MOL False True 2011 CC(C)(C)Cc1c[nH]c(C(C)(O)Cc2ccc(-c3ccc(F)cn3)c... CHEMBL240 - CHEMBL1672351 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL1672352 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 5.380 2.97 3.63 4.24 3 CHEMBL1672352 367.46 3 2 ... SQDJZWNPXIGNRP-UHFFFAOYSA-N MOL False True 2011 CC(C)(C)Cc1c[nH]c(CC(C)(O)c2ccc(-c3ccc(F)cn3)c... CHEMBL240 - CHEMBL1672352 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL1650844 [0, 0, 1, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 5.430 1.36 4.94 3.61 2 CHEMBL1650844 451.65 5 2 ... MEBYDATXPNEUSM-UHFFFAOYSA-N MOL False True 2010 OCC1(N2CCC(n3c(N4CC5CNCC5C4)nc4ccccc43)CC2)CCC... CHEMBL240 - CHEMBL1650844 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL1738705 [0, 1, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 5.590 0.91 2.61 3.88 2 CHEMBL1738705 434.57 4 2 ... WQTXERXALASGRT-GOSISDBHSA-N MOL False True 2011 Cc1c2c(n3c1CCCN1CCC[C@@H]1CNc1cc-3ccc1C(N)=O)C... CHEMBL240 - CHEMBL1738705 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL558 [0, 1, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 5.000 0.92 2.12 2.33 1 CHEMBL558 179.26 2 1 ... VLPIATFUUWWMKC-UHFFFAOYSA-N MOL False True 2011 Cc1cccc(C)c1OCC(C)N CHEMBL240 - CHEMBL558 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL363295 [0, 1, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 5.240 1.90 4.68 4.74 2 CHEMBL363295 281.44 1 1 ... UISARWKNNNHPGI-UHFFFAOYSA-N MOL False True 2011 CC(CC(c1ccccc1)c1ccccc1)NC(C)(C)C CHEMBL240 - CHEMBL363295 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL607 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 4.120 1.62 2.19 2.45 1 CHEMBL607 247.33 3 0 ... XADCESSVHJOZHK-UHFFFAOYSA-N MOL False True 2008 CCOC(=O)C1(c2ccccc2)CCN(C)CC1 CHEMBL240 - CHEMBL607 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL296419 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 8.320 4.13 5.52 5.69 4 CHEMBL296419 458.57 4 1 ... GXDALQBWZGODGZ-UHFFFAOYSA-N MOL False True 2012 COc1ccc(CCN2CCC(Nc3nc4ccccc4n3Cc3ccc(F)cc3)CC2... CHEMBL240 - CHEMBL296419 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL42 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 1, ... 5.395 3.53 3.94 3.42 2 CHEMBL42 326.82 4 1 ... QZUDBNBUXVUHMW-UHFFFAOYSA-N MOL False True 2007 CN1CCN(C2=Nc3cc(Cl)ccc3Nc3ccccc32)CC1 CHEMBL240 - CHEMBL42 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL1085398 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 1, 0, 0, ... 5.495 3.36 5.92 5.74 4 CHEMBL1085398 397.51 3 0 ... CUVRRTILZWEZCN-GOSISDBHSA-N MOL False True 2010 Cc1onc(-c2ccccc2)c1-c1ccc2cc(CCN3CCC[C@H]3C)cc... CHEMBL240 - CHEMBL1085398 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL1257577 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 1, ... 9.370 1.72 3.22 2.77 2 CHEMBL1257577 342.46 3 1 ... KNKVLWDIKQGTIB-SCAQPMJSSA-N MOL False True 2010 NC(=O)c1cccc(O[C@H]2C[C@@H]3CC[C@H](C2)N3Cc2cc... CHEMBL240 - CHEMBL1257577 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL1257687 [0, 0, 0, 0, 0, 0, 0, 0, 1, 0, 0, 1, 0, 0, 0, ... 5.700 2.45 4.30 3.99 3 CHEMBL1257687 477.55 5 0 ... XSNMDMSHDAOPPM-UHFFFAOYSA-N MOL False True 2010 Cc1ncoc1-c1nnc(SCCCN2CCC3CC3(c3cccc(C(F)(F)F)c... CHEMBL240 - CHEMBL1257687 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL1257808 [0, 0, 0, 0, 0, 0, 0, 0, 1, 0, 0, 1, 0, 0, 0, ... 6.700 2.21 4.12 3.92 3 CHEMBL1257808 477.55 5 0 ... MHPHRNFSAZNRAT-UHFFFAOYSA-N MOL False True 2010 Cc1ncoc1-c1nnc(SCCCN2CCC3(c4cccc(C(F)(F)F)c4)C... CHEMBL240 - CHEMBL1257808 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL1257448 [0, 0, 0, 0, 0, 0, 0, 0, 1, 0, 0, 1, 0, 0, 0, ... 6.300 2.84 5.50 4.95 3 CHEMBL1257448 509.56 5 0 ... NWCMUBVTFZOFKO-VBUUOAMHSA-N MOL False True 2010 Cc1ncoc1-c1nnc(SCCCN2[C@H]3CC[C@@H]2C[C@H](c2c... CHEMBL240 - CHEMBL1257448 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL1257215 [0, 0, 0, 0, 0, 0, 0, 0, 1, 0, 0, 1, 0, 0, 0, ... 6.000 3.70 6.61 5.20 3 CHEMBL1257215 479.68 5 0 ... BIJSJQXDPUAQLO-UADZTWIMSA-N MOL False True 2010 Cc1ncoc1-c1nnc(SCCCN2[C@H]3CC[C@@H]2C[C@H](c2c... CHEMBL240 - CHEMBL1257215 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL1098847 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 5.580 4.21 4.21 6.28 3 CHEMBL1098847 475.79 3 1 ... GJOOHWJFYSUFIU-NRFANRHFSA-N MOL False True 2010 CC(=O)N[C@H]1CC(C)(C)Oc2nc(-c3ccc(Cl)cc3Cl)c(-... CHEMBL240 - CHEMBL1098847 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL1258615 [0, 1, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 8.220 1.43 3.52 3.41 2 CHEMBL1258615 350.45 3 1 ... IDPGDKXBQTZRGW-RYVUZXMYSA-N MOL False True 2010 CC(c1ccccc1)N1[C@H]2CC[C@@H]1C[C@@H](Oc1cccc(C... CHEMBL240 - CHEMBL1258615 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL1642183 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 5.330 3.59 3.60 3.61 3 CHEMBL1642183 404.48 4 1 ... UORXSNLDCGLILY-VQHVLOKHSA-N MOL False True 2011 COc1cc(/C=C/c2nc3sc4c(c3c(=O)[nH]2)CCC4)ccc1-n... CHEMBL240 - CHEMBL1642183 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL594615 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 7.850 2.08 3.83 3.84 2 CHEMBL594615 416.37 4 3 ... QQKFLUBSTABOJV-UHFFFAOYSA-N MOL False True 2009 CS(=O)(=O)Nc1ccc(CCCNCCNc2ccc(Cl)c(Cl)c2)cc1 CHEMBL240 - CHEMBL594615 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL570593 [0, 1, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 7.490 1.40 3.90 1.60 3 CHEMBL570593 446.54 6 3 ... BKMZXLKUUMOTKA-XMMPIXPASA-N MOL False True 2009 CC(C)(Cc1ccc2ccccc2c1)NC[C@@H](O)COc1ccc(CCC(=... CHEMBL240 - CHEMBL570593 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL590280 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 1, 0, 0, 1, 0, ... 6.490 1.88 2.29 1.94 2 CHEMBL590280 452.55 8 0 ... YIDUAHHKCUXUPG-UHFFFAOYSA-N MOL False True 2010 CCCOCCn1c(=O)c(N2CCN(CC)CC2)nc2cnc(-c3ccc(OC)n... CHEMBL240 - CHEMBL590280 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL1270062 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 5.950 1.21 2.29 3.21 2 CHEMBL1270062 390.40 5 1 ... XOMDFOOFZKLOQX-UHFFFAOYSA-N MOL False True 2010 N#Cc1nc(CCCN2CCC(O)CC2)cc(-c2cccc(C(F)(F)F)c2)n1 CHEMBL240 - CHEMBL1270062 CHEMBL240 Homo sapiens 165
... ... ... ... ... ... ... ... ... ... ... ... ... ... ... ... ... ... ... ... ... ...
CHEMBL240 - CHEMBL3289443 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 4.770 -4.26 -1.71 1.37 1 CHEMBL3289443 436.57 6 0 ... GFUMOPVVRFRDRF-UHFFFAOYSA-N MOL False True 2014 COC(=O)N1CCC(C)(CN2CCC3(CC2)CN(S(C)(=O)=O)c2nc... CHEMBL240 - CHEMBL3289443 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL3289444 [0, 1, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 5.560 -3.50 -0.98 2.09 1 CHEMBL3289444 464.62 6 0 ... GKQPPHRQSZDMNP-UHFFFAOYSA-N MOL False True 2014 CC(C)OC(=O)N1CCC(C)(CN2CCC3(CC2)CN(S(C)(=O)=O)... CHEMBL240 - CHEMBL3289444 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL3289811 [0, 1, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 4.780 4.87 5.92 3.38 3 CHEMBL3289811 442.82 6 2 ... QAKLYMPRDNHSCY-UHFFFAOYSA-N MOL False True 2014 Nc1nc2ccc(OC3CCOC3)nc2n1CC(O)c1ccc(C(F)(F)F)cc1Cl CHEMBL240 - CHEMBL3289811 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL3290344 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 4.130 -1.50 0.62 0.70 2 CHEMBL3290344 446.50 7 1 ... KTXPVNWIGGZAFK-UHFFFAOYSA-N MOL False True 2014 COc1cnc2ccc(=O)n(CCN3CCC(NC(=O)c4cnc(C)c(C#N)c... CHEMBL240 - CHEMBL3290344 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL3287928 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 6.200 6.15 6.15 6.52 4 CHEMBL3287928 458.96 4 0 ... NYBOJRFENCLMIM-UHFFFAOYSA-N MOL False True 2014 CS(=O)(=O)c1ccc(-c2nn(-c3ccc(F)cc3)cc2Sc2ccc(C... CHEMBL240 - CHEMBL3287928 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL3286734 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 5.700 5.89 8.75 2.86 3 CHEMBL3286734 463.55 6 3 ... JVHSVVSSADEQAX-UHFFFAOYSA-N MOL False True 2014 Cc1csc(-c2ccc(N)c(NC(=O)c3ccc(N4CCC5(CC4)CNC(=... CHEMBL240 - CHEMBL3286734 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL3290340 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 4.160 1.56 1.67 1.25 2 CHEMBL3290340 420.48 6 1 ... KUAZYFBXEKPOMK-UHFFFAOYSA-N MOL False True 2014 Cc1ncc(CNC2CCN(CCn3c(=O)ccc4ncc(F)cc43)CC2)cc1C#N CHEMBL240 - CHEMBL3290340 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL3291062 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 4.800 3.14 4.70 2.17 2 CHEMBL3291062 442.46 4 1 ... GDDXUDHMUFTXTL-QDMKHBRRSA-N MOL False True 2014 Cc1onc(C(=O)N2[C@H]3CC[C@@H]2C[C@H](Nc2cc(=O)n... CHEMBL240 - CHEMBL3291062 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL3289792 [0, 1, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 4.220 2.41 4.75 1.66 2 CHEMBL3289792 255.68 3 2 ... BHVJFZCDKTUUOM-UHFFFAOYSA-N MOL False True 2014 Nc1nccn1CC(O)c1ccc(Cl)cc1F CHEMBL240 - CHEMBL3289792 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL3287739 [0, 0, 0, 0, 0, 0, 0, 0, 0, 1, 0, 0, 0, 0, 0, ... 4.500 1.41 1.41 4.47 4 CHEMBL3287739 642.72 8 3 ... HHMPSPSPFJQPAI-MKPDMIMOSA-N MOL False True 2014 Cc1cc(C(=O)N[C@H]2CC[C@@H](NC(=O)c3cc(F)cnc3Oc... CHEMBL240 - CHEMBL3287739 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL3289798 [0, 1, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 4.600 0.65 0.65 4.55 3 CHEMBL3289798 399.77 3 2 ... FOYATTRUCTWKBC-UHFFFAOYSA-N MOL False True 2014 Nc1nc(-c2ccc(F)cc2)cn1CC(O)c1ccc(C(F)(F)F)cc1Cl CHEMBL240 - CHEMBL3289798 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL3290346 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 4.160 1.67 1.82 0.52 2 CHEMBL3290346 433.51 8 1 ... LTEIHSGLROBHGJ-UHFFFAOYSA-N MOL False True 2014 COc1cnc2ccc(=O)n(CCN3CCC(NCc4cnc(C)c(C#N)n4)CC... CHEMBL240 - CHEMBL3290346 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL3290345 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 4.920 -10.31 -5.56 1.27 2 CHEMBL3290345 448.52 8 1 ... YNFJCLBTMRTMBB-UHFFFAOYSA-N MOL False True 2014 COc1cnc2ccc(=O)n(CCN3CCC(NCc4cnc(OC)c(C#N)c4)C... CHEMBL240 - CHEMBL3290345 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL3290338 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 5.280 -2.88 1.87 1.86 2 CHEMBL3290338 426.51 6 1 ... IKUSSXYCSOMLNJ-UHFFFAOYSA-N MOL False True 2014 Cc1nc(CNC2CCN(CCn3c(=O)ccc4ccc(C#N)cc43)CC2)cc... CHEMBL240 - CHEMBL3290338 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL3286736 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 6.210 4.41 4.41 2.63 3 CHEMBL3286736 461.49 6 3 ... BRPCQVRPLNOXLB-UHFFFAOYSA-N MOL False True 2014 Nc1ccc(-c2ccc(F)cc2)cc1NC(=O)c1ccc(N2CCC3(CC2)... CHEMBL240 - CHEMBL3286736 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL3305005 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 6.220 3.32 3.36 2.88 3 CHEMBL3305005 493.53 8 2 ... BCOYDHFZZXSZFA-UHFFFAOYSA-N MOL False True 2014 COc1ccc2ncc(F)c(CCC34CCC(NCc5ccc6c(n5)NC(=O)CO... CHEMBL240 - CHEMBL3305005 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL3289806 [0, 1, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 1, ... 4.910 2.81 3.72 3.73 3 CHEMBL3289806 454.88 6 2 ... ZQMUEFCLRDQIPA-UHFFFAOYSA-N MOL False True 2014 CN1CCN(c2ccc3nc(N)n(CC(O)c4ccc(C(F)(F)F)cc4Cl)... CHEMBL240 - CHEMBL3289806 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL3290347 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 4.890 5.15 5.28 1.18 2 CHEMBL3290347 433.51 8 1 ... IIJVDKDQMHKCMR-UHFFFAOYSA-N MOL False True 2014 COc1ccc2ncc(=O)n(CCN3CCC(NCc4cnc(C)c(C#N)c4)CC... CHEMBL240 - CHEMBL3290347 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL3289442 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 5.440 2.67 2.67 1.71 1 CHEMBL3289442 450.59 6 0 ... CPSGCDLKARETBW-UHFFFAOYSA-N MOL False True 2014 CCOC(=O)N1CCC(C)(CN2CCC3(CC2)CN(S(C)(=O)=O)c2n... CHEMBL240 - CHEMBL3289442 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL3287930 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 6.130 5.55 5.55 5.53 4 CHEMBL3287930 440.92 5 1 ... SITUIEYOPZHJJE-UHFFFAOYSA-N MOL False True 2014 CC(C)(O)c1cnc(-c2nn(-c3ccc(F)cc3)cc2Sc2ccc(Cl)... CHEMBL240 - CHEMBL3287930 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL3305167 [0, 1, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 4.740 4.02 4.02 1.91 3 CHEMBL3305167 509.53 9 3 ... JWCUKLIKGBNEKA-WOEOTAOXSA-N MOL False True 2014 COc1ccc2ncc(F)c(C[C@H](O)C34CCC(NCc5ccc6c(n5)N... CHEMBL240 - CHEMBL3305167 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL3287932 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 5.600 3.43 4.70 5.63 4 CHEMBL3287932 460.93 5 0 ... MKBBGPWJTNSQAC-UHFFFAOYSA-N MOL False True 2014 CS(=O)(=O)c1ccc(-c2nc(-c3ccc(F)cc3)oc2Sc2ccc(C... CHEMBL240 - CHEMBL3287932 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL3290343 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 4.480 -1.23 -1.24 -0.25 1 CHEMBL3290343 432.52 6 1 ... VRFGHMZCFXVNNY-UHFFFAOYSA-N MOL False True 2014 Cc1ncc(CNC2CCN(CCn3c(=O)ccc4c3ccc(=O)n4C)CC2)c... CHEMBL240 - CHEMBL3290343 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL3289807 [0, 1, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 5.460 3.80 5.13 4.15 3 CHEMBL3289807 420.22 5 3 ... LMUKORAVEXWMPG-UHFFFAOYSA-N MOL False True 2014 Nc1nc2ccc(NCC(F)(F)F)nc2n1CC(O)c1ccc(Cl)cc1Cl CHEMBL240 - CHEMBL3289807 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL3287926 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 5.810 -0.39 2.72 4.79 3 CHEMBL3287926 344.82 4 1 ... ZYGYGZWDRYFARC-UHFFFAOYSA-N MOL False True 2014 Clc1ccc(Sc2c[nH]nc2-c2ccc3c(c2)OCCO3)cc1 CHEMBL240 - CHEMBL3287926 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL3290342 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 5.000 2.83 2.94 1.57 2 CHEMBL3290342 432.52 7 1 ... YFMQHUHDMJCXEB-UHFFFAOYSA-N MOL False True 2014 COc1ccc2c(ccc(=O)n2CCN2CCC(NCc3cnc(C)c(C#N)c3)... CHEMBL240 - CHEMBL3290342 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL3286436 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 5.600 2.47 2.59 1.63 2 CHEMBL3286436 456.54 7 1 ... LVXBUMWPFFTWIQ-UHFFFAOYSA-N MOL False True 2014 COc1cc(C#N)c2ccc(=O)n(CCN3CCC(NCc4cnc(C)c(C#N)... CHEMBL240 - CHEMBL3286436 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL3287929 [0, 0, 0, 0, 0, 0, 1, 0, 0, 0, 0, 1, 0, 0, 0, ... 5.280 5.55 5.55 5.03 5 CHEMBL3287929 431.90 5 0 ... DMWASDIKEOIMDD-UHFFFAOYSA-N MOL False True 2014 Clc1ccc(Sc2cn(-c3cccnc3)nc2-c2ccc(-c3ncon3)cc2... CHEMBL240 - CHEMBL3287929 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL3299132 [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 6.870 2.47 2.98 2.27 1 CHEMBL3299132 309.72 5 1 ... HFARBHYZTFLIOC-UHFFFAOYSA-N MOL False True 2014 O=C1NC(=O)C(Cc2coc3ccc(Cl)cc3c2=O)S1 CHEMBL240 - CHEMBL3299132 CHEMBL240 Homo sapiens 165
CHEMBL240 - CHEMBL3287218 [0, 0, 0, 1, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, ... 5.160 1.52 2.20 3.15 4 CHEMBL3287218 512.67 5 0 ... ZIUDADZJCKGWKR-AREMUKBSSA-N MOL False True 2014 Cc1cc(-c2ccc3c(c2)CC[C@H]3N2CC3(CCN(C(=O)Cc4cn... CHEMBL240 - CHEMBL3287218 CHEMBL240 Homo sapiens 165

4703 rows × 34 columns

In [14]:
fingerprint_data = []
for index, series in sub_df.iterrows():
    fingerprint_data.append((series["CMP_CHEMBL_ID"], series["FINGERPRINT"]))
len(fingerprint_data)
Out[14]:
4703
In [23]:
def GetDistanceMatrix(data,metric,isSimilarity=1):
    """
    Adapted from rdkit, because their implementation has a bug
    in it (it relies on Python 2 doing integer division by default).
    It is also poorly documented. Metric is a function
    that returns the 'distance' between points 1 and 2.
    
    This is fixed in RDKit 2019.03.01
    Data should be a list of tuples with fingerprints in position 1
    (the rest of the elements of the tuple are not important)

    Returns the symmetric distance matrix.
    (see ML.Cluster.Resemblance for layout documentation)
    """
    nPts = len(data)
    num_pairs = int(nPts*(nPts-1)/2)
    res = np.zeros(num_pairs ,np.float)
    nSoFar=0
    for col in range(1,nPts):
        for row in range(col):
            fp1 = data[col][1]
            fp2 = data[row][1]
            if fp1.GetNumBits()>fp2.GetNumBits():
                fp1 = DataStructs.FoldFingerprint(fp1,fp1.GetNumBits()/fp2.GetNumBits())
            elif fp2.GetNumBits()>fp1.GetNumBits():
                fp2 = DataStructs.FoldFingerprint(fp2,fp2.GetNumBits()/fp1.GetNumBits())
            sim = metric(fp1,fp2)
            if isSimilarity:
                sim = 1.-sim
            res[nSoFar] = sim
            nSoFar += 1
    return res
In [16]:
distance_matrix = GetDistanceMatrix(fingerprint_data, metric=rdkit.DataStructs.TanimotoSimilarity)
distance_matrix
Out[16]:
array([0.93577982, 0.9       , 0.91044776, ..., 0.9127907 , 0.9375    ,
       0.90070922])

Now we need to mangle this flat distance matrix into a sane square one. The indices of $(\text{row}, \text{col})$ are at $\frac{(\text{col}\times(\text{col}-1))}{2} + \text{row} $ in the flat matrix.

In [17]:
sq_distance_matrix = np.empty([len(fingerprint_data), len(fingerprint_data)])
for row in range(len(fingerprint_data)):
    for col in range(row + 1):
        index = int((col * (col - 1)) / 2) + row
        if row == col:
            sq_distance_matrix[row, col] = 0.0
        else:
            sq_distance_matrix[row, col] = distance_matrix[index]
            sq_distance_matrix[col, row] = distance_matrix[index]
In [18]:
numerical_cols = [sub_df.columns[pos] for pos, item in enumerate(sub_df.dtypes) if item in [np.float64, np.int64]]
new_data = sub_df[numerical_cols].to_numpy()
dimensional_data = np.array([row[0] for row in new_data])
print(dimensional_data)
mapper = km.KeplerMapper(verbose=1)
graph = mapper.map(dimensional_data, X=sq_distance_matrix, precomputed=True, cover=km.Cover(n_cubes=35, perc_overlap=0.2), clusterer=sklearn.cluster.DBSCAN(algorithm='auto', eps=0.40, leaf_size=30, metric='precomputed', min_samples=3, n_jobs=4))

[6.74 6.1  6.26 ... 5.28 6.87 5.16]
KeplerMapper(verbose=1)
Mapping on data shaped (4703, 4703) using lens shaped (4703,)

Creating 35 hypercubes.

Created 110 edges and 263 nodes in 0:00:00.243320.
In [19]:
# Visualize it
mapper.visualize(graph, path_html="map-dataframe-test.html",
                 title="Map Dataframe Test", color_function=dimensional_data)
IFrame("map-dataframe-test.html", 800, 600)

Wrote visualization to: map-dataframe-test.html
Out[19]:

How do we actually extract meaningful data from this list? Time to visualise it!

In [20]:
mols = [Chem.MolFromSmiles(sub_df.iloc[i]["SMILES"]) for i in graph["nodes"]["cube2_cluster0"]]
from rdkit.Chem import rdFMCS
res =rdFMCS.FindMCS(mols)
newmol = Chem.MolFromSmarts(res.smartsString)
In [21]:
def draw_molecule(molec, molsize, highlight_atoms=None):
    rdDepictor.Compute2DCoords(molec)
    drawer = rdMolDraw2D.MolDraw2DSVG(molsize[0], molsize[1], highlight_atoms=highlight_atoms)
    drawer.DrawMolecule(molec)
    drawer.FinishDrawing()
    svg = drawer.GetDrawingText()
    display(SVG(svg.replace("svg:", "")))
In [22]:
for index, node in enumerate(graph["nodes"]):
    mols = [Chem.MolFromSmiles(sub_df.iloc[i]["SMILES"]) for i in graph["nodes"][node]]
    mean_bioactivity = np.mean([sub_df.iloc[i]["BIOACT_PCHEMBL_VALUE"] for i in graph["nodes"][node]])
    if len(mols) > 1:
        max_substructure = rdFMCS.FindMCS(mols, ringMatchesRingOnly=True).smartsString
        mol_smarts = Chem.MolFromSmarts(max_substructure)
        highlight_list = [mol.GetSubstructMatches(mol_smarts)[0] for mol in mols]
        print(node, mean_bioactivity)
        display(SVG(Chem.Draw._MolsToGridSVG(mols, highlightAtomLists=highlight_list)))

cube2_cluster0 4.46
O N O N NH S O O N O O N Cl Cl NH N N O NH2 O N N N 
cube2_cluster1 4.516666666666667
N Cl O N N O F N NH2 NH O N O NH N N O O OH NH N O NH O Br 
cube2_cluster2 4.407000000000001
O NH N N N N S N NH2 N F O O OH N O NH N N NH N O O F O NH N N NH N O O F N O N O OH O N N N N 
cube2_cluster3 4.413333333333334
F F F NH N NH N N O O NH O N N H O O NH O N Cl H 
cube2_cluster4 4.4366666666666665
NH O O O O HO O O O N OH O O OH HO O N N N F F F NH2 N 
cube2_cluster5 4.4430000000000005
N N Cl N NH F N O OH OH N OH O N O NH O O O O O HO N N O Cl Cl N NH O O O N O OH N 
cube2_cluster6 4.493333333333333
Cl N N NH NH O O O NH N O N S O N O N N NH N NH O O 
cube2_cluster7 4.463333333333334
O F F N N O N O Cl O N N F O OH N O N N O F 
cube2_cluster8 4.45
O N N O Cl N Cl N N NH N NH Cl N F N O NH2 Br O O 
cube2_cluster9 4.452
N O N S N N O N N N N N O N N N S N O N N N O NH N NH F F F NH N HO O O N N N O NH N 
cube2_cluster10 4.4399999999999995
N O OH F N S O O F N O NH NH O NH HO N N N F N O O HO 
cube2_cluster11 4.405
O N NH N N N NH2 O O NH F F F N F F F NH N OH N S N O F F F Cl N F 
cube2_cluster12 4.466666666666666
O N N F F F N O N N N O O NH O N N F F F H 
cube3_cluster0 4.5566666666666675
NH F N N N Cl N N N NH O N N F F F O Cl N O NH N O 
cube3_cluster1 4.544
N Cl O N N O F N N N NH O O F O O O N N N F F F O NH2 NH O N O NH N N O O OH NH N O NH O Br 
cube3_cluster2 4.596666666666667
O N N NH N N N O N N N N N O O NH S O O N N O NH F N 
cube3_cluster3 4.592
N N NH O NH O F N N NH N N N Cl F O O NH N N O O N+ O O- N NH O NH O F F N N O N N N NH2 N 
cube3_cluster4 4.616666666666666
O NH N O O NH O F O O NH N O N H2N O NH N Cl N N N NH 
cube3_cluster5 4.596666666666667
O N NH O S O N N NH N O N Cl S O O N 
cube3_cluster6 4.587999999999999
S O O N N F N HO O N F N Cl N N NH NH O O O NH N O N S N O N N N S O O O NH N S F 
cube3_cluster7 4.596666666666667
N N N N N S N N H2N O N N NH O NH S O O O N O NH NH S O O O N N N O O NH O F F F O NH O F F F O N N 
cube3_cluster8 4.543333333333333
O N N O Cl N Cl O N NH O O F F F N O F N N NH N NH Cl 
cube3_cluster9 4.587142857142857
N O N S N N O N N O N Cl Cl NH N N N O N H2N O N N N F NH Cl F O S O O O N N N F F F F NH Cl O N N H2N O NH F N N 
cube3_cluster10 4.62
NH N O NH HO O NH F O N NH OH F F Br N N N N O N N 
cube3_cluster11 4.56
O N N N N NH Cl F NH O NH Cl N O S O O N N N S O O 
cube3_cluster12 4.58
O N NH O N N N N O O O O O O O N HO OH O O NH OH OH O N OH OH N N H H 
cube3_cluster13 4.59
NH N N N Cl N O F N NH O N S O O N Cl N N N N N N O F F F Cl N O O NH O N F H 
cube3_cluster14 4.596666666666667
N O N N S N N O O N N O N H2N N F N N O N NH O NH N NH F F F N O OH N O N F F F N N N N O H2N O NH N Cl N N N NH O N N N N N N N O 
cube4_cluster0 4.762499999999999
O O N N N N O N O Cl Cl NH O O N N N O NH S O O N H NH O NH F NH O N N 
cube4_cluster1 4.7525
O O N N N N NH NH O NH N F N N N F N NH O N F N F N O NH2 O O O N N N N N Cl O NH N N 
cube4_cluster2 4.733846153846154
NH F F N N N Cl N O N O N NH S O O N N NH NH2 O N F N O N N O NH S H2N N O NH N O F F F N Cl N O Cl Cl NH N O N N N N N F F F N F N N O N O OH O N N N H2N O NH N Cl N N N NH F O F F F Cl N NH N N O NH N H2N O N N N N N O O N O O O O N O NH N N 
cube4_cluster3 4.766666666666667
NH F N N Cl N N H2N O N N N F NH Cl F O O N N N N Cl O NH Cl N 
cube4_cluster4 4.7124999999999995
N O Cl Cl NH O N O N NH N N N O NH2 O N N N N O Cl N O N O N N F 
cube4_cluster5 4.736666666666666
N O N F F NH2 F F N N NH O N N N O N N N N N N Cl O 
cube4_cluster6 4.767045454545454
N N NH O F F F F O S O O NH2 S NH O N NH O NH N N N S N N N O N N S O O N N F N HO O N F N N N N S N N OH O NH N OH O N O N O N N F F F NH2 O N O N N H H O N N F F F N N O N N O NH O OH N N O N F Cl NH H H N N O NH NH O O N O N NH O O F F F N O N N NH O N N O NH Cl Cl O N NH2 N H2N N N O N O OH O N N N O Cl N NH N O O Cl N O NH N N S O N O NH O F F F O N F F O N NH2 N O O O N O N Cl O NH N N O O N N N N N Cl O NH N N 
cube4_cluster7 4.713333333333334
O S O O O N N F F F N F F F N N NH NH2 O F N F N N N N N O N N N NH 
cube4_cluster8 4.718
H2N N N N N S N N H2N NH O N NH N N O NH O F F N Cl N N NH N O NH O F H2N O N N N F NH F 
cube4_cluster9 4.756666666666667
NH N N N Cl N O N NH2 O NH F F N OH O O N N NH N O O 
cube4_cluster10 4.744545454545454
NH F O N O N F F NH2 F F O NH N N O O N N N O NH NH2 N N O N N O N O N S N N O N O N N NH N O O O NH F Cl N N N O N O N N NH N NH O O F O O N+ O NH O F F F O N O 
cube4_cluster11 4.6866666666666665
NH N NH O NH N O NH O HO Cl NH Cl 
cube4_cluster12 4.786666666666666
N O N NH2 F F F N N O N O N N NH N O O OH O N O N NH O N F F H H 
cube4_cluster13 4.776666666666666
O NH O NH O F N N NH N O O N F OH NH N NH O O O N 
cube4_cluster14 4.753333333333334
O N N F F F N OH N N O N N O O N HO N N N N F F F O NH N 
cube4_cluster15 4.776666666666666
O OH N O F N OH O NH O N N F N O NH O N N N S 
cube4_cluster16 4.7
NH2 N O NH O O N N NH O HO N O N N N N N O 
cube4_cluster17 4.741999999999999
OH N NH2 O S N N F F F N N NH O NH N N F F F OH N N N N NH O N N N N O N O NH O N N N N NH N N N N O NH O N O N N NH O N N N N O O N N N N Cl O NH N O NH N N O N N N N N O NH NH NH N N N N F 
cube4_cluster18 4.723333333333333
N O N S N N N N NH2 NH O N NH N O OH O HO H H 
cube4_cluster19 4.75
OH N NH2 O S N N F F F O HO N O N OH N N N N O N N N O N N N F F F N N 
cube4_cluster20 4.823333333333333
O N O O S N O N F F HO N N O S O O N N S F 
cube4_cluster21 4.756666666666667
O N N F O HO H O O N N O N+ O- N NH O O NH F F F N N 
cube4_cluster22 4.766666666666667
O NH N NH NH N N F F F N N OH N F F F O NH N N O O OH N N 
cube4_cluster23 4.7749999999999995
N NH O NH N N N N N F O O N N O NH2 N O O O N N N H2N N 
cube4_cluster24 4.786666666666666
N N Cl N NH F N O N N O N S O NH NH NH N N N N 
cube4_cluster25 4.753333333333333
NH N O NH OH N N N N N N O O N F F F F 
cube4_cluster26 4.778333333333333
OH N N N N N O N O O O N N NH N NH O O N 
cube5_cluster0 4.961874999999999
O NH2 N N H2N NH O N NH N O N O N S N N N N N N N N Cl Br N N N S NH2 NH O O N NH N N N N O F NH O O F F F N Cl N NH O N N NH N Cl N N N O N NH O N N N F O N O O N OH F F NH Cl Cl O N O HO N NH O NH O F F F N O NH O F F F O N N N F F F O F N N N S O NH OH N NH N O OH N S O O Cl Cl F 
cube5_cluster1 4.9393951612903235
O S O N F N F F O NH HO N N F F F S N O N NH N N N O N O N NH N N O H O N O N NH S O O O O NH N Br N N N N NH O NH F NH O NH N N N F F F N N N O N O O N O N N O N N NH O N Cl O N OH N O N NH O N N O H NH2 S NH O N NH O NH N N O N O N S NH N O N S N N F F N NH O NH N F N N N O N O O S O O N N O N+ O- O N OH NH NH HO O O N O N N N NH N O O N O N O N O N N F N N OH OH O N N O N O O O NH O N O N N Cl NH Cl N O O O N N O N N NH NH N Cl HO O N N NH O N Cl O N O O N N NH O N Cl O N O N O N NH S O O O N N N N N O N N O N O O N O N NH S O O O N N N N O N+ O- S N NH N O N NH F N N S N N N N N N N F O F F N N O N O O N N NH O N Cl O N OH NH F N N N F F N N O N F F OH N O N NH N N O H H O NH N N NH O O F O Cl S O O N O NH O N N N NH F NH2 S NH O N NH N N N NH N O N F N N O NH O O N NH F F F O N NH N S O O N S O O N N S N N O Br N N NH N NH O O N N F F F O N O N NH2 S NH O N NH O N N N O N O NH N O NH HO Cl N N N NH O N N N O N N N N N N N NH2 O N O N N H H N O N NH N N O H O NH N N F F F N O N N N NH O N N F N NH O O O Cl Cl N N N S N OH N N N O O N N OH N N N NH S OH N N O N F Cl NH H H N O N O N N S N NH S N F NH O N N O F S N N N N N N N N S O NH N N O O N N N N NH NH2 O F N N N N Cl Cl NH2 O OH N OH O NH O O O NH O OH N F F F O O NH O Cl Cl N O O N N O H2N NH N Cl N N N N O NH O N N O NH O F F F NH N HO N O O N O F O N N O O N O F O N N N N NH O NH N N F F F N N NH O NH N F F F N N N F N O NH S O O Cl N N N N N N N N O N F NH O O N OH N NH N O O N O N O NH O F F O O N N N O N N O NH O F F N Cl Cl N OH O NH O N N F O N O NH O F F N O N N N O N N N N N NH O O F F F N O N N NH N N NH O F O N O N N N S N N N Cl N NH N N N N O N HO N NH O NH O F F F N Br N O NH N Cl Cl O NH F F F O N N N O N N H2N S O NH S O O Cl N N O Cl Cl O NH S O O N N O Cl Cl N N NH2 N N N Cl N H2N N O NH H2N O NH Cl O N OH N F F O OH N N O N N N O O F F F N N N O O N F F F F O NH N F F F H H O NH O N NH S O O O O O N N NH2 N N O N N N N O N O O O N N NH Br O NH N O N H H NH NH NH2 N N NH2 O N 
cube5_cluster2 4.9383333333333335
N O NH N N N O O O N S O O NH O NH O O N N O NH S H2N N O OH NH N O N S NH2 Cl Cl N N N N O N N N N O N N NH O O F F F N O 
cube5_cluster3 4.890000000000001
N N Cl N NH F N O O NH O N N N N O NH N N F F F NH N HO N 
cube5_cluster4 4.9190000000000005
O N NH2 O NH F N N N N N N S O O N NH O Cl Cl N NH N O N NH N N O H O NH O N NH OH F F O O S O F O O NH O NH N N NH N N O F O NH N N O N N O N N O NH Cl Cl 
cube5_cluster5 4.966666666666667
N N Cl N NH N O N N N Cl H H O NH N O N N N N O 
cube5_cluster6 4.949999999999999
O N N F O N N O H O N O N N O OH N N N N N N N N NH F F F O N O OH N N O Cl Cl N F F F O F N N O NH NH H2N N N NH2 O N Cl N N NH O N N N N N 
cube5_cluster7 4.929166666666667
NH2 O NH O N N O N NH2 O N NH O O N F Cl Cl Cl O F F F N NH2 N O N O N O OH O N N N N 
cube5_cluster8 4.968
N N N N N N N+ O- NH N N OH O N N N O NH N F F O N O NH NH N Cl N N N O Cl Cl N N O NH O OH N N N N NH2 F O 
cube5_cluster9 4.886666666666667
N N N S O N O F F F N F N O N Br 
cube5_cluster10 4.92
NH N O N F H2N N N NH O HO N Cl N O N O NH O F F Cl 
cube5_cluster11 4.8975
F F O N NH O NH HO N N S N N N O NH NH N N O N N N N N O O N N O N N N N F 
cube5_cluster12 4.966666666666667
O S O NH NH O F F F H O S O O O N N F F F F F F O N NH O O F F F N O N 
cube5_cluster13 4.88625
S NH N N NH N S O O NH O O NH O N N N O NH O N NH2 N S N S N 
cube5_cluster14 4.9366666666666665
O O N N N NH2 N NH N NH NH S NH N N F N 
cube5_cluster15 4.95
O N O N F F F O OH O N N NH N NH O O O O O N F F F N N NH OH N N N 
cube5_cluster16 4.925
O O NH O S N O H2N F O N NH O NH N N F F F N NH O N N O N F O OH F F F 
cube5_cluster17 4.9
NH N O NH OH N N N NH2 O O NH O F F F NH N N N N O O NH N N O O N N N OH OH 
cube5_cluster18 4.976666666666667
O NH O Cl Cl N F N NH O O N O OH O N Cl S O NH O F F F O N F F N 
cube5_cluster19 4.8533333333333335
O N NH F NH OH N O NH Cl N O NH N O F NH2 NH O N OH O NH Cl 
cube5_cluster20 4.927142857142857
N NH O NH O N O F N N O N O N N N Cl N NH N N N N O O HO N NH O NH O F F F N NH2 N S N O O O N NH O 
cube5_cluster21 4.922499999999999
O O S Cl N N N N NH O N N S N S N N O N N N O NH O O N N N S 
cube5_cluster22 4.927142857142856
NH N O NH HO O NH F N Cl N N N O NH N N O O N OH N N N N F N O S O O NH F Cl N N O N O O N NH2 S O N OH N F O OH 
cube5_cluster23 4.97
O O N O N N N N O N N O Cl NH Cl 
cube6_cluster0 5.073333333333333
N N N O HO O N F O NH O NH N 
cube6_cluster1 5.075209125475285
O NH2 O O F NH N N O S O N F N F F NH N Cl Cl O O O N S O O N N N N NH O NH F NH NH2 O S O O F F O NH N N Cl Cl N N N N Cl N NH N F O F F F N NH O O NH N N NH O O F O O O N O N N OH O NH N OH F O N N F O N N O H N O N NH O N N O H H2N N N N N N N N OH N NH N N O N O N O N NH2 O NH Cl Cl N N O N N O NH S H2N N O N O N NH S O O F F F O N O N S N N N N S O N NH O N NH O O F O F O N NH N NH O O F O F Cl O N NH Cl F N N N N O N Cl O N O N O NH N N N N N N NH O N N F F F F F F O N O N OH NH NH HO N N O F N O O N O N N N NH N O O N O N N N O N O N O N N O O N N N N NH N N N O S O NH NH O F F F H NH N N N N N O N NH O NH HO NH N N F F F N O N NH N N N O NH F O Cl Cl NH Cl O OH NH O N Cl N F F Cl NH N O O N O Cl Cl NH O Cl Cl N NH N N N N NH NH N Cl HO N OH Cl Cl F F F NH F O F Cl N O NH O S N O N NH N N N O N N OH N N N N F F F O N N O N O O NH O N O N NH2 S NH O N OH N N O N N F O N NH2 O N S O O OH F F F O NH N N O O N N O N O N N O N N OH H2N O S O O N F F N O NH N F N O N N O N O O S N O NH N N N N O NH O O S O O O N N F F F F F F NH F N N N F F O F N NH F O F F N NH N O F N N NH2 O O N NH N N N N N O N N N N O N S O O NH N O O NH O S N O H2N F O OH O Cl NH S O O Cl Cl N NH2 S NH O N NH N O N O N N O N O NH2 O NH S H2N O N N N N N N N OH N NH NH N N O O N N NH2 S NH O N NH NH O N O N O N O OH O O O F O F F N NH N O N O N O N N O NH S H2N N N N N N N O NH HO N Cl N F F O N O N N F F F N N O N N OH H H H H N S O O N S O O N N O NH F Cl N N N O N O N N S N N O Br N N O O N O N N NH N NH O O N O NH N O N S N F F F O N O N N O N NH N N O H O O N OH NH S N N N S O O O N N N O N N N N N N N N+ O- NH N N N O N F F H2N NH N O NH HO Cl N N Cl Cl O NH F N Br N HO O O N O OH O N Cl S N N O S N N O NH N H2N N Cl NH OH N N S O O O O Cl NH N N F NH NH F O N O NH O N N O O N N O NH N H H OH NH O NH N OH F N O N NH O N N O H OH S O O F NH O O O Cl Cl NH2 S NH O N NH O NH O N N O N O N F NH NH N N F Cl O N N H H NH NH N N N N O F O N N N O N S NH2 O O O Cl Cl N NH NH S N N NH O N N N N NH N N O S O F F N O NH S O O N N O N O N N O N O N NH NH S O O O Cl O NH O N N N N N N N N N N N N S O N N NH O N Cl O N F NH NH Cl O NH O N O N F F F N O N O N N N NH NH2 O F N N O N N N O F F F F S N N N N N S O O N O Cl Cl N HO O N F N H2N N N F F F F F F O O N NH O NH N N F F F NH N NH F F NH2 N NH2 O O NH N N OH F F F NH N O O O O NH O N N N F F F N O N O NH N Cl N N N O NH O F F F NH N N O NH O F F F NH N OH O N N O H2N NH N Cl N N N N N N O NH HO NH NH O NH HO O F N NH O Cl NH Cl H N O NH O N N O O Cl NH N N O NH O F F F NH N HO N O O N O F O N N O O F NH N N O HO N NH O NH O F F F NH O N N O NH N N N N N O O N O NH O N Cl O O O NH N N Cl Cl N N N N F N O NH S O O F F N O O N O NH N O N N N N O O N N S O O NH N Cl N N N F F F O N N N NH NH N N N NH2 N O N N O N N NH O O N N O NH O F F F F F N N O F N O N N O NH N N NH N O F O S O O N N N N O N N N N N O O NH O F F N Cl Cl O N O NH O F F O N S O O Cl N O NH O F F NH2 N NH O O F F F N NH O F O NH OH F O O NH O N N N S N O N O NH O F F O O N N O F F O N O N S O OH O N N N N N N O F F F N N N O N N N O N N O F N O N O N N O N N N N N N N N O N N N N O N NH O O F F F N O N O N N O Cl N O O N N N O NH N O N N O NH Cl Cl O NH N NH N N N N O HO O N N O Cl Cl O N NH O O F F F N O N O O OH N N O Cl Cl N O O N F N N N O NH O N N N N N O N N NH O N HO N N O N O N O OH N O N N N N O HO N O N N N N N O O N O N O HO O N N N N O N O N O N O N N N N NH2 O N NH H2N N NH N N N NH2 N N N N F F F NH2 N N F F F F N N F N N NH2 F O S NH N N O N N N N N O NH OH N O Cl Cl NH O O NH O F F F NH N OH O F F F N O NH N N F F F NH N N N NH N N O N N NH N N O N S O NH O NH2 N N N NH Cl N N Cl N NH N N N N O NH O NH N NH O Cl Cl N F F F O F NH N N F F F O F N N N Cl Cl O NH O F F F O N N N Cl Cl NH O NH2 N N N NH Cl OH N Cl Cl N O O NH O F F F N O NH O F F F O N F F N NH O NH N N O N N O N O NH NH NH2 F F F N N N NH2 F N N N O N NH2 F F F N N O NH H2N O NH Cl O N OH N F F O OH O O NH2 N O N OH N F F O OH O S NH2 N O N N N F N N N O O OH N N O N O Cl O OH HO N O H H H O O N N O O N N N N O NH O N NH S O O O N O N N O O N N N N N F NH Cl N N O NH2 N N N O N O N N O NH N N O NH N O H H O NH N F N O Br N O OH N S O O Cl Cl F NH NH N NH NH2 NH O N NH NH NH2 N N H2N O O N N NH O H2N O O N N NH N N N 
cube6_cluster2 5.0
O NH N N N F F F O N OH N NH N O O N NH NH NH2 N N NH2 O N 
cube6_cluster3 5.133333333333334
N N N N N O NH N N N O NH2 O N N NH NH2 NH N 
cube6_cluster4 5.043333333333333
N N H2N NH O N NH N NH O N N NH N Cl N N N O F N N N F F F F F F N N F 
cube6_cluster5 5.09
O N N O OH N H H H H F O F F N NH O N N N S N N O N O NH F F Cl N O NH O O S O O O N N F F F F F F F N NH F O NH S N N N N N O NH Cl Cl H OH O NH N OH F O O F NH N N N N NH O NH N F F F N N H2N N O N N N O N N O S O O N F F F N S O O O S O O N O O NH O OH N O F F F N NH O NH2 N N N NH Cl O N NH2 S OH O O O N O NH N S 
cube6_cluster6 5.14
O S O F F N N NH N N NH O F O O O O S O O O NH N S 
cube6_cluster7 5.1075
F N NH O N O N N N O NH NH2 F O NH Cl N O F F F N Cl 
cube6_cluster8 5.066666666666666
N O O N NH N N O H H O N N O N N N NH O O F F F O 
cube6_cluster9 5.0683333333333325
N N N O NH NH2 Cl O N N O N N N S O O OH 
cube6_cluster10 5.095
O N N O N O N N N O NH NH2 Cl O NH N N NH N O F O NH N N NH N O F F N N O N N O NH O O N N O F F F N N N NH2 F O N O Cl 
cube6_cluster11 5.026666666666666
OH O N N N O NH N F F O N O NH NH N Cl N N N O NH O N N O NH HO F F F 
cube6_cluster12 5.03
N N O N O N O O N NH O NH N NH F F F O N NH O O F F F N N 
cube6_cluster13 5.0633333333333335
O O N O S Cl N N N N F N O NH S O O Cl N O F F F N N N F 
cube7_cluster0 5.251470588235294
O S O F F N F F N NH O Cl O O N N N F F F N N N S N F N S N O O N O NH O N N O O N N N O NH N NH O F O S O O NH N N F NH2 N N N N NH N N N N N O N N N O O F N NH H2N O N N N F NH F O N N N O N N F O NH O N N F F F O N N N Cl N O N N NH NH S 
cube7_cluster1 5.242874015748034
N N N NH N O N Br O S O O NH O NH NH Cl Cl F N NH O Cl Cl O NH N N Cl Cl N N O N N N F Cl NH N O F O N N O N N S N F F F N N N S N N N O N N N O N N S N N F F F O N OH N N N N NH N N N N N N S N N O Br N N Cl O N NH Cl N N F N Cl O O N N F F F F F F O N O N N O NH S NH2 N O N NH2 O NH F F N N N N N O O O O S O F N N F F O O N O O N O NH N NH2 O N S O O OH F F F O N NH F O F F N NH F O F F F N NH N N N S H2N O S O O N F F O NH N N F F F N HO N O NH O O N N O N N N O O N NH O O F O NH O F N N O N O N N N F F F O NH O N NH Cl Cl Cl N O N O F N N NH2 O NH2 S NH O N O NH N N O N N F F N NH N O NH2 O NH S H2N N O N O N HO O N N N S S O O N O Cl Cl N OH O N F N O S O O O N O N N O NH N N F F F N O N O N N N O N O N N O F N N N N O N NH O Cl N N N N O N O H N O N NH N N O H H NH Cl Cl N N S N N O N N N Cl O NH2 O N N NH F F F N N N F F F NH F O Cl F N N N O NH NH2 Cl N N O O N N N N O O N F N NH O NH N N N O NH N O NH N N N N N OH O O N Cl Cl NH O OH F S O O F N NH S N O N N O N N NH S O O NH S O O N O N N S N N N N S N N O O N N N O N O N N N S N N N N H2N O NH Cl N N N NH O N NH O N H2N N Cl O N O NH O N N N N N F F OH NH O NH N N N N O F H H H2N O N N N F NH F O N NH NH N Cl N N N O O NH NH N Cl N N N NH F O NH OH F H2N O N N N F NH F F NH2 N NH O NH O F F F NH O NH OH N O F F F O N NH O NH N NH F F F O O O NH N N F F F N S O O N OH O N O NH O N Cl O O O NH N N Cl Cl N O O NH O N N N S N N NH O O N O N O NH OH O O N O NH O F F F F F O NH N N NH N O F F F F O NH N N NH N O F H H O N N F F F O N N N N N O N N N N N N F S F O NH N O F F O NH N O F F F N N O O N N O NH Cl Cl O HO F F F N N O Cl Cl O OH N N O Cl Cl N N O N N O N F O OH F F F O N O N O OH Cl O N N N N O N O N O OH N O N N N N NH O NH N NH O Cl Cl O NH O F F F NH N OH N S O NH OH N O Cl Cl NH O F F F NH O NH2 N N N NH Cl O NH O F F F O N N O NH O F F F O N O N Cl NH Cl O N O NH NH NH2 F F F O N O N Cl Cl N N O NH Cl O NH NH2 NH2 N N N N F F F NH2 N N N N F F F NH2 N O N NH F F F N N N NH2 O Cl N NH2 O N NH O NH N O F N O N N O O N N N N NH O NH OH O OH N Cl O N O N NH O NH O F F F N O N NH O NH O F F F NH N N O NH N O H H NH NH NH2 N N H2N O N N OH N NH NH S N NH O N HO O N N N N Cl Cl N 
cube7_cluster2 5.22
NH N N F O O N N H H N Cl O N O N F NH NH Cl O F NH N O NH O N N O F F F N O NH O Cl Cl N N O 
cube7_cluster3 5.244545454545454
O O O N S O O O NH N NH F N N Cl N NH O O F NH N N O NH N N N NH N N N O N N S N O N N O OH NH O N N Cl Cl O F F F N O N Cl S N N N N N O N O N OH NH S O O N O O N N O N N N N F F F 
cube7_cluster4 5.236666666666667
N N N N F F F O F O NH N N N N O F H H O N NH O NH O F F F N 
cube7_cluster5 5.236666666666667
O F NH NH O N N N N NH O F H H N NH O NH HO 
cube7_cluster6 5.235
O O O N S O O N N N N N N NH2 N NH N N O N S N N O N N O F O OH N N 
cube7_cluster7 5.272
O N N NH O O N N S N F F F N N N N O F F F N N N O N N O NH F F F N N N N O N N O NH Cl Cl 
cube7_cluster8 5.2775
NH N O N H2N N O N S N N N N O NH N O F F N O F F F N NH N NH S O O N O N 
cube7_cluster9 5.244999999999999
N N S N N O N N N O N N OH H H H H O O N N N O NH F O N O N O HO O N N N N 
cube7_cluster10 5.2825
N N N N N N NH2 N NH N N O N N N O NH F O Cl Cl NH O NH O O N N N O N O NH O N NH N NH N NH2 O N N O O F F F NH NH N N O N N N NH2 N N F F F N F F F 
cube7_cluster11 5.2475000000000005
O N NH N N NH N N S O O N N O NH O N O N NH2 N N N N F 
cube7_cluster12 5.2875
OH N O O S N N F F F NH N O Cl Cl O NH N O O F O S O O N H2N F F F N 
cube7_cluster13 5.2275
N S N N O N N F O NH N N O N N O N N N N O NH O O N N N O NH 
cube7_cluster14 5.22
N O NH O NH O NH N NH O Cl Cl O NH O F F F N N O 
cube7_cluster15 5.266666666666667
N N N N N N N N N NH N N O N N N NH HO O N NH O O F F F N N 
cube7_cluster16 5.285
N O N NH N N O H H NH O Cl F N NH O NH N NH F F F O N N S O O O NH Cl O Cl Cl N O NH N O O N Cl Cl 
cube7_cluster17 5.233333333333334
NH S O O NH O Cl Cl Cl NH Cl H O O NH O N N F F F N 
cube7_cluster18 5.1866666666666665
NH N N N N N O N NH O S NH O NH N O N F N N O O N F N 
cube7_cluster19 5.213333333333334
F NH NH F N O F H2N O N F N N N N N N N S N N O O NH N N O NH O F F F NH N OH O F F F N N N N O N O N N O 
cube7_cluster20 5.296666666666667
O N N F O N NH H N O N N NH O N Cl O O N NH O NH N O F F F 
cube7_cluster21 5.22625
O N NH N F O N O N O NH N O N N S O NH O F F F O N N F N 
cube7_cluster22 5.215000000000001
N O N O N O N N F O N O H O N N O N O H N O N O N N N N O N N N N N O O NH O F F F O N F N 
cube7_cluster23 5.203333333333333
N N O NH F Cl O F N N N NH N N NH O NH HO 
cube7_cluster24 5.283333333333333
O N N NH S O O N N S N N F F F N N N N N O O N O N N N 
cube8_cluster0 5.425238095238096
OH N N N NH N N N N N O N O H N N N Cl O O N O N NH O O F O F N N S N O N N N NH N NH NH2 N NH2 O S O O NH N F F F S O O NH N S NH F F F O Cl Cl N N Br N N N N NH N O O S O F F NH F O Cl F O S O F F N O NH N N F F F NH N N N N O N N N N Cl NH Cl H O NH NH N N N N O F F F N S O O O O N N NH N O O NH N NH S O O N O N NH O NH OH O OH N Cl O 
cube8_cluster1 5.449
O N N N N N NH S N N O N Cl N O N N S N F F F N N N N N N O NH HO F F F O N N N NH2 F N 
cube8_cluster2 5.435
O N S O NH N N NH N O N O F F F N NH F Cl O Cl Cl O N N O OH F N N O NH NH OH F F N O N NH O O N O N 
cube8_cluster3 5.3925
O N O N NH S O O O O O N S N Cl N N NH S O O N NH N NH NH NH N NH2 O N N O O F F F 
cube8_cluster4 5.4335
S O O NH O NH NH Cl Cl O NH F N Cl N N N N N Cl O O NH HO NH N N F F F O NH N N F F F N N O OH N O S N N F F F NH O N NH Cl Cl Cl N O N N NH O HO N Cl N N N N N N N NH2 N NH N N O NH N N N O NH O N O O N F F F NH N O N N N O N O NH N Cl N N N O N N NH O O O N O N N H2N N N O NH2 O NH Cl N N N NH O NH OH O OH N F O NH NH2 O N N NH H2N NH N H2N N NH F F F N N OH Cl Cl 
cube8_cluster5 5.419782608695653
O N N N F Cl O NH O NH O NH N O NH Cl N O NH Cl OH NH N N F F F Cl N N O O N O N N N Cl O N O N N NH N NH S O O N F F F O S O O N H2N N O O O N S O O O NH N Cl NH N O O N N O N N N S N N O N N O O F NH N N N Cl O N O N N Br O N S N N N N N N N N NH O N O N N S N F F F F N O N NH NH N Cl N N N O NH O F F F NH N N N N NH N NH N NH2 N O NH O NH N O F N O N 
cube8_cluster6 5.435
O S O NH N O Cl N S N N O N N O N O NH O S O NH N N F F F N N F F F N O N N N N N F F F F S N O N Cl Cl N NH N 
cube8_cluster7 5.446
NH O N O N N N N O O N F N N N N NH N N O N O NH O O N N NH O N N 
cube8_cluster8 5.3675
O N N N O O F NH Cl O N S N N O N N O N O N NH N O N N N N 
cube8_cluster9 5.412000000000001
N N NH H2N O F F F N O N OH N N NH N Cl Cl O NH O N NH N Cl N N N O O NH NH S O O Br 
cube8_cluster10 5.4475
N N N Cl NH N O N OH H H H H O N N S O Cl O NH O N O N N O N N N N N N O F F F Cl NH OH N NH O Cl Cl N N N N N N O NH F O O N NH N NH NH NH2 O O N N NH O NH N F F F O O N O NH HO N N O F O N N O F N N N O NH 
cube8_cluster11 5.4174999999999995
N O NH O NH O Cl Cl N N O NH2 N O O NH O F F F O N F F F N 
cube8_cluster12 5.406666666666666
N N O N F F F F NH H H NH2 N Cl Cl O N N S O O O NH Cl 
cube8_cluster13 5.419999999999999
N N S N O N N N O O F NH N N O O N O N N N N S O O F 
cube8_cluster14 5.4174999999999995
F F F F F F N N N Cl O O O S O F Cl N F O NH O N N F F F N N HO N NH O O F F F 
cube8_cluster15 5.476666666666667
S O N NH2 N O N O F F F N Cl 
cube8_cluster16 5.4325
NH Cl O N NH O N N O N N N N N N N N NH2 N NH N N NH N NH O F F F F O Cl O F F F N O O OH N N O O N N O NH Cl Cl N N F F F N NH Cl O F NH F F F N N N NH2 O N N OH O O O NH O N NH N O S O NH N N O F S 
cube8_cluster17 5.43375
OH N O NH N OH F N N NH O F F F F F F O S O O NH Cl O Cl Cl N N N N Cl O N O F H2N O N F N N NH2 N N N N O NH2 N N NH O N NH2 N S N F 
cube8_cluster18 5.430000000000001
O N N Cl O N O H O NH OH O Cl N N NH N Cl OH O NH NH N N N O F F F N 
cube8_cluster19 5.394
O NH OH O N NH N O NH HO NH O Cl O O N N OH NH N Cl N N N O OH Cl N N O Cl Cl 
cube8_cluster20 5.396
O NH OH Cl Cl N N F F F N N NH O N F N N O NH N O N N N N O NH2 N N NH N NH O NH N N N OH OH O F F N 
cube8_cluster21 5.43
O N N O NH O F N N N O N N N N N F F F N O O N N O N N N N 
cube8_cluster22 5.42
N N N F O N N N N N O O NH N O Cl Cl S O O N N O NH S H2N N O NH N N O NH F F N F F F N O S O O N H2N F F F N O N N F F F O 
cube8_cluster23 5.41
O NH O N N F O N F N N N O O N NH O NH N N F F F 
cube8_cluster24 5.421250000000001
NH N O NH HO NH O Cl Cl O N N N Cl N O N N S N N O N O Cl Cl N O NH N O O O OH N O F O OH N N NH2 N N NH N 
cube8_cluster25 5.396666666666666
N S O O N O N N N O N N O NH2 N N OH Cl Cl 
cube8_cluster26 5.38
N N O NH N N F F F N N N N N N NH O NH N O O F F F 
cube8_cluster27 5.3999999999999995
N N N N N N N N N NH N N N S N F F F N N N N H N Cl Cl H 
cube9_cluster0 5.5441666666666665
O N N N O NH O N N O N N S N F F F N N O N N N N N F F F F O OH N N N N F N N N N F N N O O F 
cube9_cluster1 5.616666666666667
O NH O N Cl Cl Cl N N N N N N N NH N N NH N NH NH N NH2 O 
cube9_cluster2 5.57090909090909
O N NH O Cl Cl NH N NH NH2 N NH2 O NH F F F O Cl Cl H2N O NH O O O OH NH O O N OH F N S O O NH O NH O N N N N N OH N S O O O N O S O O F N F F F N Cl 
cube9_cluster3 5.616666666666667
N N O F F F O N N H H N N N N NH2 S NH O N N O OH N 
cube9_cluster4 5.574999999999999
O NH N N S NH Cl O Cl Cl NH2 N N NH O N O S O O NH N H2N N 
cube9_cluster5 5.608181818181818
N N O O NH N NH O F O N O NH N S O O N O O F F F N N S O O F F F F F OH O N N F F F NH F N O NH N O O Cl O NH N NH NH N NH2 O NH2 N N N N F N O N N H2N F F N Cl S O N N S O O N F O S Cl N 
cube9_cluster6 5.587368421052631
H2N S NH O N NH N N N Cl N NH N N N N O N NH O N N F F F O N NH O NH O NH N F O NH Cl N O N N F N OH N N N NH O NH N Br N N O NH O N Cl N O N N N Cl O O O O N O F F F NH N O NH N N F F F N N N Br O N S N N N N O NH O F F F NH N NH O O N O N N N N S O O F N O S O O F N F F F N O N N H2N F O N N N N O O N O N N N N Cl N O 
cube9_cluster7 5.571
N N O O N F N NH O NH N N N O NH N N S N O N N N O N N O N H N N N NH N N O S O N NH N O N N O HO N S N O Cl N O N N NH O N N O NH O N O F F F 
cube9_cluster8 5.559642857142857
N NH N Cl O N N S HO N O N S N N N N N N N N NH N N N N F F F F O N N H H O O F N N N O- S+ F N F N F N S O O O N N O F Br N N O N S N N N O HO N O N N N N N O N HO N S O O O NH OH N O Cl Cl NH O NH N Cl NH S O O N O NH O O N N O N N 
cube9_cluster9 5.53
N N O O N F N N O N N S N O F F N N N O S O O N N N S O O F F F 
cube9_cluster10 5.576129032258064
O O N O NH N N F F F O N O N NH O O F O F N O N N S NH F F F N NH Cl O Cl NH F O O Cl Cl O Cl Cl NH O O N NH N N S N N O Br N N O NH N N F F F N N O N N N S N Cl N S O N N O N O O O N S O O N N NH O HO N Cl N NH2 Cl O NH N N N N N N O N O H H NH O N N N N O N OH O NH N N F F F O N NH O NH N NH F F F N O NH O F F F NH N OH F O N O NH N Cl N N N O O N NH O NH N N F F F F F F N O NH O N N O N N NH O O O N O S O O N N N F O N N N F F N O N S N N N N O N S N N N N N HO N NH O F F N N N NH N F NH NH N N N O NH N NH S O O O O N N N N 
cube9_cluster11 5.546428571428572
N F NH O Cl Cl O N NH O N N N Cl O S O NH N O Cl NH N NH NH N NH2 O O NH NH N N N N O F F F O NH OH N O Cl Cl NH N F F F 
cube9_cluster12 5.57
N O N NH N N O H H HO O N N Cl Cl N Cl N N N F O Cl N O N N N NH O F F F N N N N S N S N N O N N N N N S N N N N 
cube9_cluster13 5.536666666666666
S O N N N NH N NH N F NH2 N O N O F F F 
cube9_cluster14 5.5737499999999995
N N N N Cl F O F F F N NH N N O O NH N O N NH O NH O F F F O N N NH N O N O N N N NH2 F N N NH N NH2 N O O N N O N N N N 
cube9_cluster15 5.63
O S O F N F F OH N OH S N O Cl N N NH O N 
cube9_cluster16 5.53
O N N N F Cl O O N N O O N S N N Br N N N N NH N O 
cube9_cluster17 5.546666666666667
N N N O NH N Cl Cl N N NH2 O 
cube9_cluster18 5.5475
N O NH F F F N N S N O N N N NH2 N NH N O N N O 
cube9_cluster19 5.504999999999999
O Cl O F F F N O O OH N N O O N N NH Cl O F NH F F F N N N NH2 O 
cube9_cluster20 5.569999999999999
NH N N N Cl Cl N N N N N S O O N NH N N O Cl N O N N N N O O N 
cube9_cluster21 5.563333333333333
O N O O N O OH O O O N N N N N F O N O N 
cube9_cluster22 5.59
NH Cl O N N N S N Cl N S O NH O O N N N O H 
cube9_cluster23 5.593333333333334
N N S N N S N N O N F N N N N O OH N N Br N O 
cube10_cluster0 5.8020000000000005
NH Cl Cl N Br O N S N N N N NH Cl O N OH N NH O NH O F F F O OH N N O Cl Cl 
cube10_cluster1 5.756
O N N N N O O N NH S O O F N N S N N O N N N O N NH O N N N S N N N N N N N N N O O O O N N N N NH O F H H N N NH S NH O O N Cl N N NH N O N N N O N N N N N O N N O O 
cube10_cluster2 5.754700000000001
N O N N S N F F F N NH N NH O N F F F O N O N N HO N N O N N N O F F F O N N H H N N O F F F NH O O N N N N N N N N O NH2 S NH O N NH N O N S N N N N O N N N NH O O N N S N O F F F N N N O N NH N N N S N N N N N S N Cl O N N N NH O Cl Cl N N O F F F O N N H H S O O NH O OH N Cl Cl F F F N O F O N N N O NH N H H O N NH NH O NH O Cl Cl N N N N N N N N NH N N N O N N S N F N O NH N Cl N F F O O Cl N N N NH2 O O N N H H S O N N N O Cl Cl N O N N O N N O O N N N N N N N N S N N N N O O N N S N N N N N NH2 S NH2 N O N O O S O F F N F F O N S N N O N N O N N F F F NH N Cl F N N O NH N N NH NH2 O O H O NH N NH NH HO O NH N N H2N O O N Cl N NH N O O N O NH O F F N Cl Cl N N O N N N O NH HO N N N N O N OH O Cl N N F Cl NH O NH N N O NH Cl Cl NH2 N N N F F 
cube10_cluster3 5.789999999999999
N O N N S N N N NH NH O NH N Cl N O Br 
cube10_cluster4 5.7700000000000005
NH2 S NH2 N N N N N F NH N N N F F 
cube10_cluster5 5.75
N N S N Cl N N N N S N N N N N N O NH OH N O Cl Cl NH 
cube10_cluster6 5.8
N O N N S N F F F N O NH O N N F F F F N O N N NH O N 
cube10_cluster7 5.7219999999999995
N N N Cl O S O O N O NH N N F F F O N N O O N S N OH O NH N N F F F O N O NH O Cl 
cube10_cluster8 5.761999999999999
F N O NH F F F N O N N O F NH S O O O NH OH N O Cl Cl NH O N N NH O F O O N N O O N N 
cube10_cluster9 5.753333333333333
N N O N N N N H2N NH N NH NH N NH2 O O N S O O N 
cube10_cluster10 5.7375
N NH O F F F F F F O N N N N N N N O S O O N OH F F NH F Br N O 
cube10_cluster11 5.706666666666666
N N O N O N N S N N F F F N N N N N N N N N 
cube10_cluster12 5.736111111111111
N N O F N O N N S N F F F F N O N S N N O N N Cl N N O O O N N N Cl H H O NH OH Cl N N F F F NH2 S NH O N N N N N O OH N N Br N O N NH N F NH NH N 
cube10_cluster13 5.786666666666666
O NH N N F F F N N N N O N N N OH O O NH N OH F 
cube10_cluster14 5.736666666666667
S O O NH O OH NH Cl F N N Cl N O N N S 
cube10_cluster15 5.7385714285714275
O N N N O NH N S O O O Cl N S N N N N O NH2 O O N H H O O N N NH N S N O Cl Cl N NH N O O NH N O F F 
cube10_cluster16 5.739999999999999
OH N Cl N NH2 N NH O F N N Cl S O N N 
cube10_cluster17 5.783333333333332
N N NH H2N O F F F N N O OH NH O NH Cl O NH Cl N O NH NH NH2 N N NH2 O N 
cube10_cluster18 5.7875
N Cl N S O NH Cl HO N N F F F NH N NH H2N N NH2 O NH2 N S O NH OH Cl NH 
cube10_cluster19 5.705
O N N N Cl O O N NH N N S H H NH NH Cl O O NH N F N N N N 
cube10_cluster20 5.795
O NH N N N S N N N O N N OH O NH N Cl N N N O N N N O N O OH O N N 
cube10_cluster21 5.756666666666667
N NH O N N N O N N NH Br O Cl Cl Cl O N OH NH O NH N F F F 
cube10_cluster22 5.745
O N NH O Cl Cl N N N S N F F F N H O N O O N O OH O N OH S N O Cl N O OH O OH N Cl O N HO 
cube10_cluster23 5.683333333333334
NH F O O Cl Cl N N N N O Cl N Cl O N N O N 
cube10_cluster24 5.746666666666667
H2N O O O O NH O F F F NH N O O O NH N N O 
cube10_cluster25 5.713333333333334
S O O NH N N O N N N Cl N N S 
cube10_cluster26 5.746666666666666
NH2 O N O N S N N NH N O N N O N O O NH N O F F 
cube10_cluster27 5.752000000000001
O S O F OH N F S O O NH N H O O O N N N F F N O N N N N O NH N N NH N O Cl F 
cube10_cluster28 5.773333333333333
NH Cl O F Cl NH O NH N N N O N O N O NH F F F N N 
cube10_cluster29 5.7799999999999985
N N O NH N N N N NH O F F N N NH O NH 
cube10_cluster30 5.753333333333333
F O F F F N NH NH S O O N N N NH N NH N 
cube10_cluster31 5.733333333333333
N O NH O N Cl Cl Cl N NH O O N N N NH NH O N S N NH O Cl N 
cube10_cluster32 5.739999999999999
N NH O Cl Cl NH N S O O O Cl Cl S NH2 NH O N NH O O N 
cube11_cluster0 5.92
N O N N S N N H H NH2 O N O N S N O N N Cl O N O N S N N F F N O S O O O N N N F F F 
cube11_cluster1 5.905833333333334
O N N N NH Cl O Cl F N O NH F F NH N N O N N F F F N NH O F N O N S N N N 
cube11_cluster2 5.903999999999999
O N N N N O OH N NH N N N S NH N O Cl Cl S N N N N O NH NH NH HO 
cube11_cluster3 5.918666666666667
N NH S O O H N NH O O N N O N N N N S N N F F O N N S O O NH O OH NH Cl NH2 O O N F H H S O O NH NH H N N N N N S N N N S O NH O N Cl Cl Cl N NH N NH O N N F F O F F F N N S O O N O N F F F O S O F F N F F O N O N N N N N O N NH F N NH N N O NH N N Cl Cl 
cube11_cluster4 5.917
NH F F F N N N O Cl NH Cl O N F O N N OH F F F S O O N N O F F F OH N Cl N N O OH HN O NH Cl O NH Cl N N N S S H2N N N N OH S NH O NH F N+ Cl Cl N NH N NH2 N 
cube11_cluster5 5.947
N N N N N O O N N N N NH2 O NH O O N F O O NH Cl OH O OH N Cl O NH N O 
cube11_cluster6 5.950000000000001
O N N O N N NH O Cl Cl N N N Cl O H F N O N N N N 
cube11_cluster7 5.923333333333333
O NH O N N F O NH F F F F F F N O HO O N O NH O Cl 
cube11_cluster8 5.960000000000001
N NH O N F N F N O F F O F F F N N S O O N N NH F F F O N N O N S O NH N NH F F F NH N 
cube11_cluster9 5.906000000000001
NH N NH O N F F F O N N Cl S O O N N N N Cl O H NH2 S NH O N N OH N N NH O NH O N Cl Cl Cl O NH O F F F NH N O O O NH OH F F N NH F O N N O NH OH F F F N N O NH HO F F N N N O F O NH HO F F N N N F 
cube11_cluster10 5.919558823529412
O O I O N I F N S N N N N O Cl N O O N O OH F NH NH N N F F F F F F O N N S N N F F F O N N N S N F F F N N N N H N Cl N S NH F F F O Cl Cl N N F F F N N N N N S N N N N N N S N N N N O N O N N S N Cl N N O N N S N F F F N N N N F O S N N N N N NH O N O N Cl N N N N N N S N N S N Cl Cl N N O NH N NH F N O S N N N N N O N N NH O N OH N F O S Cl N N O O N O N N O NH OH F F F N O N F N O N N O F F F N N F N O N S N N N O N NH S N N O Cl F N O N N N S N O Cl Cl N NH N N N O N OH N N N N O S NH2 N S O NH OH Cl NH 2H NH F F F N N N N+ O O- 
cube11_cluster11 5.880000000000001
NH O Cl Cl O NH F F F N N N NH N O NH N NH2 N NH2 O N N N F F F NH N+ O O- 
cube11_cluster12 5.84
N N N O N N OH O NH N Cl N N N O N N N O N O OH O N N 
cube11_cluster13 5.884
N N N S N F F F N O H2N S NH O N NH N NH F F F O Cl Cl F F F N N N O O N N N H2N N S 
cube11_cluster14 5.951666666666667
N N N HO F F F N S O O NH NH H N NH O N N N O N N NH2 S NH2 N NH O N N F O O NH OH N O Cl Cl NH O S O O N 
cube11_cluster15 5.924000000000001
N N S N N F F F O N N N N N N N NH N O N N S N NH O N N F F O N N O F O N N 
cube11_cluster16 5.955
N F S O O F N NH2 O O N N H H S O O NH N F N N N NH O F 
cube11_cluster17 6.0
N O N N S N O F F F N N O N S N N O N N N N N S O O O NH OH N O Cl Cl NH O 
cube11_cluster18 5.966666666666666
O N N F F F N Cl N O N S N N N N NH NH NH2 N N NH2 O N 
cube11_cluster19 5.903333333333333
O S O OH N F O NH O N N F N NH O O N O N H H 
cube12_cluster0 6.099999999999999
N N O N N S N O N N N N N O N O N F F F N N N N 
cube12_cluster1 6.075333333333334
O N O N NH N N N N N S N N F F F N Cl N N F F F F F F O O N N N Cl Cl N S N N N N N O N S N N N N O O N N F F F N N N O NH N N N N N N F H H O O N N O F F O N O N N NH O N N N N O NH O O N N O O NH N N O N N O O N 
cube12_cluster2 6.045999999999999
O NH N Br N Cl Cl O F F F N N S O O N N NH F F F O N N O N S O O O NH O NH N O NH Cl N O N N NH O N N 
cube12_cluster3 6.0875
N N N N NH O S O O NH O OH NH Cl Cl N N N O NH NH O NH N 
cube12_cluster4 6.0875
N N N S N F F F N N H N NH S O O NH NH F O NH OH F N O Cl 
cube12_cluster5 6.036666666666666
NH O N N N Cl O NH O N N F F N N O N N N O F F F N N S O O OH F F F Cl N N S N O O NH Cl Cl N N N 
cube12_cluster6 6.069090909090908
N N S N N O N N N N S N N F F F O N N O N O N N N O N Cl N N N NH O N N N O N N H2N F N O N S N O NH N NH N N N NH O N N F O O O N NH O F F O O O NH N O F F F F F F F F O NH OH N O Cl Cl NH O S O O N 
cube12_cluster7 6.064444444444444
O NH O N O N O O NH O NH N O NH Cl N N N S O F F F N N NH Cl O F F F F N O N S N N N N O O N NH O F F OH O F N N Cl Cl N N O NH N N Cl Cl NH NH NH2 N N NH2 O N 
cube12_cluster8 6.1274999999999995
O NH NH Cl O Cl N N S S O NH O NH O OH N Cl O 
cube12_cluster9 6.1066666666666665
N N S N N O N N NH2 O F O N H H N N N F 
cube12_cluster10 6.065555555555555
NH O O Cl Cl N O N N S N O F F F N O S O NH NH F F F H N N F F F N N N O NH NH N N N N N N N N N F N N O N NH N F N N O N S N N O N N N N O N S N O Cl N O O O NH N N O O NH OH F F N Cl Cl O NH HO F F N N O N F N NH S N O N O N N N N N N S O O O NH OH N O Cl Cl NH O O NH NH S O O N OH H H 
cube12_cluster11 6.039999999999999
O N N O OH F F F F F F O N O N N NH2 N N NH NH 
cube12_cluster12 6.109999999999999
N N N N N N NH O N N O N N N N N O 
cube12_cluster13 6.073333333333333
O O O N N O N N N F F F N NH F F O NH N O F F F F F F F F 
cube12_cluster14 6.0
NH2 O O N N H H S O O NH N F N N N NH O F 
cube13_cluster0 6.226666666666667
NH2 N N NH O N S O O O O N N N F S O O N N F S Cl 
cube13_cluster1 6.241666666666667
N N O N O F F F N H H F N O N N N O N N NH F F F F F F N N N S N N O N N S O O Cl S O N O O N O O NH O Cl 
cube13_cluster2 6.279999999999999
N O NH N N Cl Cl N NH O NH O NH F N O N N S N F F F F N N N O N O F F F N H H N O N N N O 
cube13_cluster3 6.246666666666667
O NH N N N S NH2 O O N H H O O O NH O NH N O NH Cl N 
cube13_cluster4 6.272857142857143
N O N S N N N N OH NH O N O Cl N NH O NH N N N O N N NH O N N O N N O NH N F F F Cl Cl N N N S N F F F N S N N N N NH O O Cl 
cube13_cluster5 6.22
N N N O N N Cl O O H2N NH O N NH N N O N N S N Br N O N O N F F F N N N N 
cube13_cluster6 6.25
N O N N S N F F F N H H O NH HO OH N OH NH Cl O Cl 
cube13_cluster7 6.289999999999999
N N S O N N N F F F NH N+ O O- O O OH N Cl O NH 
cube13_cluster8 6.27
O N N N N N O N N S N F F F N H O NH HO N F F F NH 
cube13_cluster9 6.223333333333334
O N NH N N NH O NH N N N O O OH N Cl O NH 
cube14_cluster0 6.419999999999999
N O N N S NH F F F N HO N N O F N F F N O N N N O 
cube14_cluster1 6.456
O O O O HO O O O N HO OH O O NH OH OH N S N N F F F N N O N S N N N N O N O N OH H H H H N O N N S N O F F F F F N N 
cube14_cluster2 6.386666666666667
O NH N N N S N O N O S O O N NH O NH Cl O NH Cl N F 
cube14_cluster3 6.45
N NH N NH Cl Cl N NH N O N O N O O NH O Cl Cl N O F N O N S N N N F F F 
cube14_cluster4 6.41
N N N N N Cl Cl N Cl O N O N N N N N O N O NH N O H H 
cube14_cluster5 6.456666666666666
N F F F O N O N N O N N N N N NH N F NH NH N 
cube14_cluster6 6.403333333333333
NH O N NH Cl Cl Cl N O N N N NH O O OH N Cl N NH Cl 
cube14_cluster7 6.41
N NH O NH S O N O NH Cl N N N Br N O N NH O Cl Cl N 
cube15_cluster0 6.616
O NH F F F F F F N N F N N N N S N N S N N N N N O O NH N N N S N N O N O Cl N 
cube15_cluster1 6.58125
N O Cl N NH N N O H O Cl N N O O F F F F F F N N O O N N N O NH NH2 N N 
cube17_cluster0 6.98
N HO N N N F O O NH N F F O NH N F F F F F F F F 
cube18_cluster0 7.05
N N S N N F F F F F O N N O H2N Cl O NH N O F O N N O O O NH N O NH S O O NH S O O 
cube21_cluster0 7.576666666666665
NH OH O O OH N NH N N Cl Cl Cl O N+ O- N N N O N 
cube21_cluster1 7.56
N N N N N O O N O O N Cl NH O N N O O O 
cube23_cluster0 7.946
S O O NH NH NH Cl Cl N N F Cl N O N O O N O NH2 O H H N NH F F OH
In [ ]: